Holidays and Happenstance
by enserio
Summary: It became a new normal that they would run into each other once or twice a year, drawn together at Luke and Lorelai's for family holidays and events. What does this new normal look like for Jess and Rory? Banter, late night conversations, old friends becoming new friends, hints of tension and accidental touches. Literati slow burn, scattered moments after S7.
1. Chapter 1: Thanksgiving 2007

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 **Chapter 1**

 **Thanksgiving, 2007**

The car shuddered as he pulled to a stop at a gas station somewhere on I-95 in Connecticut. He had crossed the state line from New York a while ago, but the old car wasn't going to make it all the way to Stars Hollow without a fill up. It was a perpetually needy heap of rusted metal on sagging wheels. He was a self-admitted idiot for continuing to try to get it to run.

He slammed the car door shut and fiddled with the pump. When the hose was propped up, and gas slowly began trickling into the tank, he leaned against the car door and pulled out his battered phone.

Luke had texted him. _Where are you?_

He responded quickly. _In CT. Should be there soon._

Jess had been roped into Thanksgiving with Luke and Lorelai when Liz announced that she and TJ were heading to a medieval feast somewhere in nowhere Pennsylvania. Jess didn't care much about Thanksgiving; he normally spent the holiday with a bottle of whiskey and a book, but Luke had a different vision this year. He wanted a proper Thanksgiving with Lorelai and her family, and had even offered to host at the diner. Jess was informed by a gruff phone call that it would mean a lot to Luke if he attended. So, though his friends at the printing press tried to coax him into staying for a proper bachelors' dinner of take out and six packs, he ended up packing late Thursday morning, firing up the old car, and heading towards his old, bumbling little town.

He sighed, and checked the pump. The bottle of whiskey would still be there when he got back. Hopefully the guys wouldn't burn the shop down in the meantime.

He returned the pump, crumpled his receipt, and tossed it in the trash. He was already running late.

When Jess pulled up in front of the diner he was faintly surprised to see how many people were milling about inside. He exhaled, leaning back in his seat. He didn't particularly want to go in and get the usual scowls from the goodhearted townspeople that would never forgive him for his seventeen-year-old self's leather jacket and cigarettes. But he had made a promise to Luke, and perhaps it was time that he began to reacquaint himself with the eccentric crowd that was Stars Hollow. He was older, more mature, and didn't really give a damn what anyone thought of him. And if Luke's unbearable happiness over the phone was any indication, he and Lorelai were going to be together for a very, very long time. Jess may as well get used to visiting more.

He locked his car and slipped the keys into the pocket of his dark jeans. Then he hurried up the steps, opened the door, and slipped quietly into the chaos.

Jess was struck immediately by a familiar mix of smells: coffee grinds, burgers, Clorox, and by the chattering din that filled the small space. He winced at the sensory overload.

It appeared as though Luke and Lorelai had decided to host a combined Thanksgiving for their families, and then half the town showed up as well. Jess recognized Lorelai's parents, holding court over by the cocktail cart, and April tucked up on a stool reading a book. There was a long, decorated table with 14 or so places set by the window, but various townspeople crowded every other seat, happily chatting and gossiping and nursing coffees. Jess stood on his toes, straining to see Luke in the crowd.

He spotted his uncle by the phone, looking entirely panicked. Jess ducked between tables and sidled up to the counter.

"Jess!" Luke gave him a quick, one-armed hug, then gestured at the tables, slightly manic, "Look at this! Can you believe it? Kirk overheard Lorelai on the phone and put up flyers announcing 'Family Thanksgiving' at Luke's to the town. I'm going to kill him!"

Jess raised his eyebrows. "You can't kick them out?"

"Believe me, I've tried," Luke scowled and gripped the counter. "I can't get anyone to leave. They said they didn't make plans because they were going to come here. I don't have enough food! And I'm not going to feed them _our_ Thanksgiving dinner. Parasites."

Jess saw Kirk sitting at one of the tables, knife and fork in hands, staring expectantly at Luke. Jess couldn't help but crack a half-smile. "Can you get Lorelai to do it?"

"She's trying," Luke pointed. Jess saw Lorelai pleading with Babette, gesturing at the kitchen hopelessly. Luke groaned, "I don't know how we're going to get out of this. Our food is ready but we can't eat it with all of them in here!"

Jess glanced at him. "Well, you do have plenty of food here."

"Sure, but not Thanksgiving food. Not our food. Kirk requested gluten-free stuffing, can you believe him? I said no and he handed me a recipe! Ten minutes ago! The nerve."

Jess clapped him on the shoulder, "Well, beggars can't be choosers. Tell them they can have cheeseburgers or they can leave. Cheeseburgers _to go_."

Luke thought about it. Before he could respond, Lorelai popped up in front of the counter. "No luck hon, they're sticking to us like glue. I tried to explain that we're not a soup kitchen, that this is for family, and Babette gave me those big eyes and said, 'Of course sweetie, we are your family!' Luke, if I don't get to eat at least nine helpings of Thanksgiving food, there's no telling what I may do. I'm desperate. There will be consequences. Dire consequences."

She paused, and turned to Jess. "Hi, troublemaker. Glad you could make it." Then she turned back to Luke, but before she could continue ranting, he cut her off.

"Jess says we could give them cheeseburgers to go. What do you think?"

Lorelai went from fake-tearful to grinning in half a second. "Brilliant. Love it. Send them on their way with greasy food. Can you cook that many that fast?"

Luke was already firing up the grill. "Sure. Jess can help me."

Jess rolled his eyes, but went ahead and slipped off his dark gray blazer and hung it on a hook. He headed back towards the freezer. Five minutes in Stars Hollow and he was back to being a waiter and pissing off townspeople. This town was an incorrigible broken time machine.

It didn't take long for him to pick up his minimum wage labor habits again. Within half an hour he and Luke had boxed up twenty or so cheeseburgers and stuffed them in boxes with triple servings of fries. Lorelai scooped them up and handed them out as people left. "Thanks for coming you all, sorry our oven broke!" She patted Kirk on the shoulder, "Here you go, Kirk, lettuce bun for you."

The chattering crowd filed out more or less amicably, dispersing into the town square for a picnic style Thanksgiving. When the place was empty (Luke and Lorelai had to escort Taylor out policemen-style) Luke slammed and locked the door.

"Well heavens," Lorelai's mother had a hand on her hip, "do you always have that many vagrants in here? Where do they all come from? Shouldn't you call the police?"

"Mom, I would, but the cop was here too. Gin martini please?" Lorelai looked pointedly at the cocktail cart. Her mother shot her a withering look, but primly turned around and began fixing a drink for her daughter.

Jess took in the remaining group as he washed and dried his hands. He knew almost all of them: Lorelai's parents, April, Sookie, Jackson, and a couple kids that he assumed belonged to them.

There was no sign of Rory, but he wasn't sure he minded. The last time he had seen her had been the painful evening in Truncheon, when she had come to him confused and scattered and desperate. He had sewed up that part of his heart neatly in prose and cauterized it with alcohol, long before her visit to his print shop, but it still ached occasionally when provoked. Her kiss in Philadelphia and subsequent spill of panic and emotion – admitting to being in love with her douchebag boyfriend - had hit him like an unexpected punch to the gut. It was probably easier not to see her.

"Anyone else?" Emily handed Lorelai a martini. She raised her eyebrows at Jess. "You?"

"Whiskey, neat," he requested. He shrugged on his blazer. He needed a drink.

Lorelai's father toasted him, "That a boy."

Jess leaned against the counter by April, swirling his whiskey, as the group hurried to draw curtains and pull the contraband Thanksgiving food from the not-broken oven and the other cabinets and cupboards that Lorelai had thrown things into. "Don't worry kids, we're only twenty minutes or so away from eating," Lorelai assured them as she pulled a ziplock bag of dinner rolls from where they had been taped underneath the stool next to April.

April shook her head, not looking up from her book, "This is ridiculous."

Jess sipped his whiskey. "This is Stars Hollow."

The flurry of activity continued until Jess and April were eventually shooed into seats at the table by Sookie. Jess felt most comfortable next to April, who continued to read her book under the table and did not bother to engage him in conversation. He watched the madness, vaguely amused, observing the endless banter.

Finally, everyone drew up chairs. Lorelai lit the candles. She sat next to Luke, but there was an empty chair to her right.

Luke cleared his throat. "I, uh, I want to thank all of you for being here with us today. It means a lot to me and Lorelai to have all of you here together, for this meal, without Kirk."

"We love all of you," Lorelai beamed.

Luke raised a glass, "A toast, to family and friends, and -"

There was a quiet knock on the door that cut him off mid-sentence. Luke jumped up from the table, "I swear to god, Kirk, if that's you, I'm going to kill you."

They all watched as he peeked through the curtain, and then visibly relaxed. "Rory!" he quickly opened the door, "we didn't think you were going to make it until later!"

"Hi Luke," she stepped in, giving him a hug, "Yeah, I managed to sneak off the trail early and grab a morning train. Did I make it in time?"

"You sure did," he grinned and re-locked the door, ushering her towards the table.

"Hi kiddo!" Lorelai leaped up and gave her daughter a hug.

"Hi everyone," Rory waved at the table, "hi Grandma, hi Grandpa." She settled in her chair, smiling at the group, and caught eyes with Jess.

Jess was unsurprised at how calm he felt. They had left things awkwardly last time, but it was not through any fault of his own. A three-day binge on alcohol with his roommates had been enough to forget that night, forget his ex-girlfriend, and re-seal that piece in him that had been battered by her visit.

He tipped his glass to her, and offered a half-smile. She returned it, but he could see her happiness fall ever so slightly, a crease of guilt appearing between her brows.

Luke resumed his toast, buoyed by Rory's arrival. Jess watched his uncle, appreciating his sentimental toast, and then raised his glass to join in and cheer the holiday.

The dinner flew by in a hazy blur of merry conversation, unexpectedly good food (Jess forgot how talented his uncle and Sookie were at these things), and a few more glasses of whiskey. Lorelai's father, Richard, took it upon himself to continuously refill both of their glasses and engage him in a long and detailed discussion of book publishing and the effects of future online sales. Jess rather enjoyed speaking with him. By the time the pecan and pumpkin pies were being passed around, Richard had pulled Emily aside no less than three times to say, "Emily, did you here what this young man just said? Remarkable, this business!"

Jess caught Rory's eyes on him only once, after her grandfather's second exclamation, but did not linger to maintain eye contact. He was beginning to feel the heady influence of alcohol, and could feel the tenseness in his shoulders unknotting. He was starting to suspect that he liked this odd, close-knit crowd of Luke and Lorelai's.

By the time dinner ended the sun had long gone down, and the chill of the dark, late autumn night caused Luke to pull out a space heater. Lorelai had her feet in his lap, her fourth slice of pie balanced on her armrest. The group rearranged more or less into a circle of chairs. Jess made a pot of coffee (to try to balance out the excess whiskey in his bloodstream) and drank a mug of it on a high stool by the counter, watching the group, catching snatches of various conversations.

Rory was perched on a chair leaning close to her mother, the two of them cheerfully gossiping. Sookie and Jackson seemed intent on trying to dissuade their children from using their crayons on the floor. Luke chatted with Lorelai's parents, more at ease than Jess had ever seen him with them. Despite himself, he enjoyed the warmth of the moment.

Soon enough Sookie and Jackson took their children home and to bed, and Emily and Richard bustled out the door after a series of goodbyes. Richard shook Jess' hand firmly, "I hope to see you again young man, I have some more questions. And it's always good to know a good publisher."

Jess returned the shake, "Thanks for the evening and the whiskey."

Richard winked and let Emily pull him out the door.

Jess and Luke started doing the dishes together, cleaning up and letting the three women – Lorelai, Rory, and April – drink coffee and catch up. Jess swore he could still see a corner of April's book under the table.

When most everything was cleaned up, and Luke was resting against the counter, waiting for the dish washer to cycle through, Jess clapped him on the shoulder and told him he would be outside for a minute. He slipped out the door and into the cold, dark autumn night.

This town would never change. He leaned against the wall of the diner, looking out at the gazebo and the square, all done up with festive holiday decorations. In his pocket he toyed with his lighter and thought of the pack of cigarettes tucked somewhere in his glove compartment.

Jess heard the door creak open again. He glanced up and saw her familiar figure. "Hey."

Rory stepped down. "Hey. Was hoping to catch you for a minute."

"Consider me caught," he looked back towards the town square, "what's new, Gilmore?"

She shrugged and leaned against the wall also, making sure to leave at least two feet of space between them. She wasn't wearing her coat, and crossed her arms tightly to preserve warmth in her sweater. "Crazy day, huh? Mom told me about Kirk and Babette and everyone. Thanks for helping to save their Thanksgiving."

He didn't try to suppress his sarcasm. "I was thankful for the opportunity to kick all of them out."

Rory smiled, "I figured."

They lapsed into quiet for another minute. Jess was now toying with both his lighter and his car keys in his pocket, urging for a smoke but trying his best not to, because he knew he was an idiot for keeping cigarettes in his car anyway when he was trying to quit.

"So, what's new with you?" He turned towards her, leaning his shoulder into the wall, focusing intently to try to wrench his thoughts away from his glove box. "You graduate yet? Where are you these days?"

"Yep, graduated," she raised herself a few centimeters taller, "I'm kind of all over right now, working on Senator Obama's campaign. Different city every few days. You know, living that vagabond _On the Road_ existence we always dreamed of, except this one has a lot more red white and blue streamers and targeted bumper sticker slogans."

Jess snorted. "A regular Kerouac you are. Do you hitchhike on the campaign busses?"

"Oh yeah, sleep under the stars in Iowa, urge my boss to continue to go west, the whole bit."

Jess couldn't help but grin. He was helpless to a woman who could quote Kerouac.

"What about you?" she looked up at him, blue eyes calmer, more relaxed from their banter, "how's Truncheon? Write another book yet?"

"There may be one in the making," Jess replied casually, "but to be honest, I only think it isn't garbage when it's four in the morning and I'm high on alcohol and sleep deprivation. I can't see it living beyond the pages of a notebook where hopefully no one will ever have the misfortune of reading it, let alone paying for it."

"No way," Rory exclaimed, "come on, Jess, let it live. Every artist is his own worst critic. I'm sure it's amazing, just like _Subsect_."

"It is what it is," Jess shrugged.

"You know, I have worked as an editor," Rory tilted her head, smiling, "you could send it to me. I would be happy to let you know how truly, ridiculously talented you are."

Her flattery was sweet, but he shook his head. "You'd have to give me the most brutal, cutthroat, Yale-editor feedback in your repertoire. None of that confidence boosting or hand holding. If you didn't send it back shredded, I'd be frankly disappointed."

"Alright," she agreed, her smile growing, "so much red pen you couldn't read the original words. A scathing editorial review. A dream-crushing blitzkrieg of brutal, honest criticism."

"That's better," Jess nodded. "Alright Gilmore, keep a look out on the road. You may stumble across a manila envelope in Iowa somewhere that's full of alcoholic rambling begging for a proper beat down."

"Deal," she offered her hand.

He hesitated for a millisecond, and then pulled his hand from his pocket and shook her hand. Her skin was icy cold.

"You should get inside," he shoved his hands back in his pockets, "you may freeze to death and then I'll have no editor."

"I'm fine," she re-crossed her arms. He watched her bite her lip, hesitating. Then she sighed. "I actually have been meaning to talk to you for a while, to apologize for last time."

Jess stayed quiet, his eyes on her, waiting. Snatches of their last conversation in Truncheon floated through his memory, but he ignored them. Idly, he wondered if she was still with that blonde boyfriend that she had wanted to cheat on but couldn't. He wouldn't be surprised.

"I was an idiot, a total idiot, and I'm so sorry for dragging you into my mess. You really didn't deserve it," she shifted, uncomfortable, "I've been wanting to reach out to you, to get rid of the awkwardness, but I didn't want to do it over the phone or anything."

He watched her carefully. She seemed to stumble, unsure how to phrase what she wanted to say.

"You're just – you're more important to me than how I made it look that night. I shouldn't have used you, or visited you alone, and I want you to know how entirely my fault that entire situation was. And -"

"Rory," he interrupted, "it's really okay."

She bit her lip, staring at him.

"Seriously," he shifted his weight, "I get it. It wasn't the greatest thing you've ever done, but people do crazy things when they're in pain and in love."

Rory appreciated this. She glanced back out at the gazebo. "Yeah, they do."

"So how did that end up?" Jess asked after a pause. He had other biting commentary that he could have added, but restrained. Rory had lived with his running opinions on her boyfriend before; he knew that she could fill in the blanks of his less-than-impressed opinions.

She sighed, "Recently ended. More or less amicably. He wanted more than I was willing to give at this point in my life."

Jess read the subtext. He let it sink in, contemplative.

"Anyway," she stood up straight, pushing herself off of the wall, "I really just wanted to let you know that I'm sorry, and that I appreciate you a lot more than what I showed in Truncheon. Chalk it up to a continuation of Rory: The emotionally stupid college years."

He chuckled. "We all have those years. Some of us are just more emotionally stupid than others."

There was a long pause. He gripped his lighter in his pocket. "Rory, I think that there is a lot that we could apologize to each other for. Let's just agree to be less stupid to each other in the future."

She nodded, her blue eyes fixed on his. "Agreed."

Jess held the eye contact for a long moment, searching her. Then he pushed off the wall, gave a light tug on her sleeve, and moved past her, back towards the door of the diner. "See you inside."

He could feel her eyes on him as he opened the door and re-entered the warmth of the diner, but it didn't bother him. The shredded teenage part of his heart was quiet, still, unaffected. Perhaps this was what adulthood looked like to him now, being able to be calm and sensitive around a person that had once made him feel like he was suffocating and choking on his own desperate, unquenchable emotion. Jess appreciated Rory's apology, but he didn't feel changed because of it. He had closed her door years ago, and locked it with an extra deadbolt after her painful visit to the publishing house.

When she came back inside the diner she gave him a small smile, but kept her space and distance. Jess allowed himself to sink a little deeper into his whiskey. He flipped her words over in his head, musing.

Later that night, as he lay in his old bed in the apartment above the diner, drowsy from Thanksgiving food, whiskey, and nostalgia, he pictured her in her old room at Luke and Lorelai's house. They were both too old for this, too old for these old rooms and twin beds and teenage memories.

Jess remembered her editor blitzkrieg comment, and smiled in spite of himself. Maybe he would send a chapter of his shitty writing to her, for the sake of feedback or artistic growth or masochism. Or maybe he would just run into her again at some family holiday, during all of the future instances that he knew he would be pulled back to Stars Hollow and back to Luke. He could let this be, let himself be an artist without her banter and blue eyes finding their way into the literary strings of his writing.

He rolled over and gently did his best to push Rory out of his thoughts and out of his memories.


	2. Chapter 2: Christmas 2008

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 **Chapter 2**

 **Christmas 2008**

The whirlwind month after the end of the campaign and the end of the election left Rory feeling battered, bruised, and exhilarated. She left the beat of the trail on good terms with her online magazine, flush with four different recommendation letters, the glow of being a part of a historic campaign, and a portfolio of successful articles signed _Rory Gilmore_.

Within a week of election day she rode the wave into a few different no-nonsense interviews in chic modern offices on the upper floors of lofty Manhattan skyscrapers. She brought her neatly printed resumes and tied her hair into a sensible knot on the top of her head, and smiled and used the firm handshake that her grandfather had practiced with her when she was a kid. When she called her mom to tell her that she had landed a job at New York Magazine, they screamed together and jumped around, one in Luke's diner and the other on a corner in SoHo. Her grandparents helped her with the security deposit on an apartment in Bushwick, and her mom drove up to help her collect knick-knacky furniture at different Brooklyn thrift stores and vintage sellers. They splurged on a brand new mattress at a real store after they saw a few too many abandoned mattresses on the street with vaguely suspicious stains and crawling bugs.

By the last week of November Rory was set up with her metro card, her own spotty wifi, and her neighborhood coffee shop. She knew where the cheapest bagel was between her subway stop on the west side and her office, and she had the right amount of twinkle lights strung up to eliminate the terrible overhead lighting in her apartment. She went to a few different happy hours at dimly lit village bars with the other new employees and paid interns.

Soon, the glow faded to normalcy, and Rory began to get used to the new New York life she led. Her job was anything but glamorous. As an entry-level editorial assistant, she became well-acquainted with the Starbucks baristas on her street and developed advanced copying skills. She hung out in the mail room, reloaded printer ink, signed for packages, checked her boss' email, and sent handwritten thank you notes to the authors, celebrities, and artists that someone else interviewed and wrote about.

She arrived at work early and left late, exhausted, dozing off on the subway and falling into her bed without even kicking off her shoes. Her fridge became an embarrassing combination of molding take out containers and half-empty condiments. Her dirty laundry piled so high that she was forced to buy new underwear after work one day.

When Christmas finally loomed on the horizon Rory felt a deep sense of relief, not only for her laundry, but for the chance to escape to Stars Hollow for a few days and forget the drafty New York avenues and the icy steps that she always slipped on at her apartment.

A few days before she was supposed to go home, her phone rang on her walk from the subway platform to her apartment. It was dark and bitterly cold, and she cursed at having to pull her hand out of her pocket to hold her phone up to her ear.

"Hello?"

"Hey kid!" Lorelai's cheer caused Rory to smile despite herself, "three day countdown, you ready? I'm trying to draft a takeout schedule, to hit all the favorites, but I think we're going to have to double or triple up on meals to make it all work, which I _know_ we are fully prepared for after our years and years of painstaking training."

"Fine by me," Rory reached the stoop of her building and rummaged in her purse for her keys, holding the phone with her shoulder, "did you include that new place that you were telling me about last month? The Indian/Southern combo pop up restaurant?"

"Yes," Lorelai scoffed, "what do you think I am, an amateur? That will be our second lunch on day two, right after the full and complete burger collection at Luke's. You've got to try their fried chicken samosas."

"Deal. Are you stocked up on junk food?"

"Picked up poptarts, red vines, doughnut holes, and ice cream today," Lorelai listed off, "oh, and Luke promised to supply us with a five gallon bucket of French fries as long as we let him put lettuce on our cheeseburgers the whole time you're here."

Rory managed to unlock the door and quickly moved into the hallway, slamming the door to shut out the cold behind her. "That's a heavy price to pay but I guess we can try to tolerate it."

"I'm trying to train Paul Anka to take the lettuce and hide it, but you know Paul Anka, he will not do anything that he deigns to be beneath him. Plan B will be the age old napkin trick."

"Last time Luke made us shake out our napkins," Rory pointed out, slowly stepping up the stairs to her third-floor apartment, "we have to have a more creative solution. Maybe we should watch magic trick videos. Or hire a consultant."

"Um, no thank you, lettuce up my sleeve sounds worse than lettuce on my cheeseburger. I'll just use my wily woman ways to get him to change his mind."

"Good idea," Rory unlocked her apartment door and stepped inside, flicking on the lights, "don't let me know the details."

"I'll tell you all about it on Friday," Lorelai blew her a kiss over the phone, "see you soon, let me know your train schedule. Love you."

"Love you too," Rory replied. She hung up, tossed her phone on her bedside table, and collapsed onto her bed, coat and all. Friday could never come soon enough.

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Her trip back to Stars Hollow was delayed by a snowstorm, but Rory couldn't care less once she was safely on the train, chilled fingers wrapped around a hot coffee thermos, book open in her lap. She allowed herself to disappear in fiction for the first time since her job had started eight weeks earlier. Jane Austen wasn't the most original of choices, but Rory needed something warm and familiar. _I declare after all there is no enjoyment like reading! How much sooner one tires of any thing than of a book! – When I have a house of my own, I shall be miserable if I have not an excellent library._

Rory did not quite yet have an excellent library, but she did have more books than she could fit on the bursting shelves in her little apartment. Some were classics, read so many times that the worn covers were falling off and the pages felt like fabric to her fingertips: Orwell, Kerouac, Steinbeck, Bukowski, Bronte, Wilde, Vonnegut, Woolf. Others were less worn, more rigid, their secrets not laid quite so bare, their words not quite as memorized.

Some books she kept buried on purpose. The guilty pleasure books that she pulled out when she needed the equivalent of poptarts for her brain, the books that reminded her of moments too painful or precious to bear, and a slim black novel signed by one Jess Mariano.

She remembered that her mother had told her that Jess was coming to visit Luke for Christmas this year, and shifted slightly in her seat. She hadn't seen Jess in a while now but they conversed sporadically, usually through one-sentence texts with book recommendations or short emails with brief well-wishes after one of them published something or other. To her relief, Rory felt fairly comfortable with her distant friendship with Jess. She hadn't been sure if her awkward, stumbling apology would fix the guilt she felt over using him a couple years ago in Truncheon, but if nothing else it had seemed to at least build a tentative, fragile bridge between them. At Thanksgiving last year Jess had seemed so unbothered by her apology, leaning against the wall of the diner, his dark eyes fixed on her without awkwardness or judgment. She hadn't been able to match his confident eye contact, but she had felt perfectly laid bare by his. And he had taken her apology, shrugged it away, and let everything rest between them, even going so far as to send dry-humored book recommendations to her in Iowa as a token that the bridge between them was real and not imagined.

 _This reads like a Didion ripoff, but who am I to judge characters for having too much anxiety?_

 _A lovechild of the standard bildungsroman and surrealism. I think Ernest would have hated it._

 _I'm not sure this author has ever met a real, live woman, but his stream-of-consciousness reads like he's well-acquainted with a variety of illicit substances._

She read every single one of the recommendations, and gave him a one or two sentence text review back, doing her best to stay on par with his casual humor. She looked forward to receiving them every couple months or so, sharp reminders of the literary world that she was missing due to her job on the campaign and then her job in New York. The excuses to read a decent book on the subway and craft some type of thoughtful response made her feel more like herself than she did in weeks of fetching coffee and making double-sided copies.

Perhaps this holiday she could be in the same room as Jess without the gnawing guilt that had chewed her up at the last family Thanksgiving. She knew it was in her head – no man could pull off that quality of James Dean indifference unless he truly was unbothered by it all – but Rory still felt shame over the behavior that Jess had witnessed and absorbed from her in Truncheon.

Austen would have had none of it. _My good opinion once lost, is lost forever._

Jess Mariano it seemed was slightly more forgiving.

.

.

The magic of Christmas in Stars Hollow swept Rory and her suitcase full of dirty laundry straight out of her New York blues and into the cheery joy of the snow-dusted, light-strung town. She chatted with her mom over take out containers in front of classic old movies and over large mugs of coffee at their usual table at Luke's. They snuck junk food under the table to avoid Luke's protestations and gave him big innocent smiles when he thought he heard the crackle of wrappers. Whenever they could bear the cold, they put coffee in to-go thermoses and walked the town, stepping into the familiar little shops and saying hi to all the people that Rory missed from Brooklyn.

On Christmas Eve they attended Miss Patty's holiday ballet performance dressed in their most festive and glamorous attire, like honored guests at a properly fancy gala. Rory borrowed an old gold sequined skirt from her mother, and tugged on the black heeled ankle boots that she wore to work nearly every day in the city. Lorelai resisted a boa but could not resist a shockingly scarlet shade of lipstick. "It's Santa-colored," she justified, giving Rory a sly wink.

When they arrived they hurried to their seats next to Babette. "Oh sugar, I'm so glad you're here," she patted Lorelai's knee, "Taylor kept threatening to not let me save seats in an effort to stop town cliques. I told him if there was no law then he could scram, but then he tried to take your chair!"

"Well thank you for not letting him steal my chair," Lorelai twisted in her seat, trying to spot Taylor, "besides, there is no town clique! What is he talking about? Has he been watching too many teen high school movies lately? Did someone accidentally lend him a copy of _The Breakfast Club? Mean Girls_?"

"Who knows," Babette shrugged, "you know how Taylor gets. Always trying to fix something."

Rory glanced back and saw Taylor tugging a chair away from Kirk. "No, Taylor, it's for Lulu!" Kirk pulled back, straining, "a clique can't be two people in love! No!"

Rory faced forward, hiding a smile.

The performance, a mixture of _The Nutcracker_ and something that might have been _Home Alone_ , was enjoyable enough but entirely too long, and Rory caught herself stifling yawns as the final dances revolved to a close. The ending, and the eruption of applause, jolted her awake. She clapped politely and smiled as her mother wolf-whistled the ballerinas.

"Which after party do you think we should attend?" Lorelai put her arm around Rory, giving her a short squeeze, "the cast party always has the best food but the under-21 vibe is kind of a bummer. Crew knows how to throw down but they come with the threatening possibility of being exposed to basement beer pong."

"Luke's? Coffee?" Rory suggested, sleepy.

"Excellent plan, child of mine. Caffeine first, then debauchery and revelry."

The two women left Miss Patty's in a flurry of cheek-kisses, happy-holidays, warm hugs, and cheer. They avoided Kirk, who had taken it upon himself to take Polaroid photos of all of the underage dancers and was badgering them for autographs to sell signed copies at the town fair.

The light in Luke's was on, but the sign on the front door said CLOSED in large, no-nonsense letters. Lorelai completely ignored it and pulled out her key ring. "Perks of sleeping with the owner," she told Rory conversationally, as she unlocked the door and pushed it open.

When Rory stepped in she saw Luke and Jess sitting across from each other at a table, both of them relaxed, nursing mugs, mid-conversation. They both looked up at the women when they entered.

"Honey, I'm home," Lorelai tossed her sparkling clutch in an empty chair, "coffee on?"

Without waiting for Luke's reply she bustled behind the counter, procured two appropriately bucket-sized mugs, and filled them both with the full pot of coffee that Rory was sure Luke had timed to coincide with the end of Miss Patty's show, specifically for them.

"Well, no one can say you don't feel at home here," Luke rolled his eyes, "Hi, Rory, come sit." He pulled the chair out from next to him.

Rory sat. She nodded at Jess across from her. "Hey Jess."

"Hi Jess," Lorelai called from the counter.

"Hey," he tipped his mug towards her, "Happy holidays. What's with the get up?"

"Oh right," Rory glanced down at her garishly sequined skirt, "well, we wanted to be appropriately dressed for the town ballet. Mom found this somewhere, in a closet or a trunk or the eighties."

A smirk tugged Jess' lips, but he hid it by taking a sip from his coffee mug. Lorelai placed a mug of coffee in front of Rory, and then took the remaining empty chair. She flashed Luke a smile. "You really missed out on the ballet/play."

"Oh really?"

"Oh yeah. It had everything. Romance, magic, suspense, murder -"

"Murder?"

"Yes, murder. Fake knife, red scarf for blood, the whole staged shebang. We're thinking four, no, five Tony nominations minimum, wouldn't you say Rory?"

"Definitely, and that's with us expecting at least two snubs due to the political inclinations of the costume designer," Rory agreed.

"Besides, you could have gone out with us dressed like this," Lorelai tossed some of her hair back to show off the shoulder pads that accompanied her red dress, "aren't you sorry you missed it?"

"Not really," Luke snorted, "I've had enough of that ballet. The ballerinas have been trying to hide from Miss Patty behind the counter in here to avoid rehearsal. Very high-pitched, lots of drama."

"Well it wouldn't be a show without drama," Lorelai said. She turned to Jess. "What's new with you? Luke said you're here because TJ had an accident?"

Jess nodded, "He tried to joust without pads. He's out of the hospital now, but Liz didn't want to do anything big for the holidays. I think handling Christmas for Doula is stressful enough without me hanging around."

"Wow, jousting," Lorelai couldn't help but crack a smile, "is this a regular thing? Like instead of going to the gym he goes to the joust? Does Doula have a little jousting cheer outfit?"

Rory spared Jess from having to respond and interrupted. "How old is Doula now anyways?"

"Almost two, I think," Luke said, "sounds like they're having a hell of a time trying to keep the kid from killing herself. Liz never took baby-proofing very seriously. Jess swallowed a box of screws once. Ate them like popcorn, doctor was furious."

Jess grimaced. "Great."

"But she's doing better with Doula right?" Lorelai pressed, "she took Rory's old baby gates from the house. I'm sure there are no power tools or home improvement supplies laying around anymore."

"She's doing fine," Luke said, "This is her second Christmas, no permanent scars yet, happy home, decent though admittedly bizarre parents."

"Bizarre parents are the best parents," Lorelai leaned forward, "did I tell you the thematic sequence I created for Rory's Halloween costumes until the age of 6?"

Rory let herself tune out the familiar story, enjoying the warmth of the coffee mug on her fingertips and the pleasant, homey vibe of the cozy diner. Snowflakes built up on the windowsill, and she settled deeper into her chair.

She glanced at Jess, as he listened to Lorelai. He looked a little different from the last time she had seen him at Thanksgiving, though he hadn't seemed to have aged at all. His hair was still a dark mess, his jawline was still dusted with five o'clock shadow. He was wearing a dark gray Henley with the sleeves pushed up his forearms, both hands gripping the mug of coffee. His dark eyes were intent on Lorelai as she exuberantly told her story, something of a smile playing at the corners of his lips.

Perhaps it was curiosity, the nosy ex-girlfriend inside her that made her take subtle glances at his familiar frame, or just the usual casual interest she took in men her age. There had always been something about Jess that peaked her interest.

He glanced at her, and she felt an inner twinge of embarrassment at being caught. She flashed him a small smile and re-focused on her mother, concentrating, listening to the story of the different obscure movie characters Lorelai had dressed her as during her infancy. Lorelai stood up and began to act out her particularly dramatic three-year-old costume, and Rory couldn't help but laugh, holding her coffee, letting herself forget everything else and be distracted by her mother's antics.

.

.

Christmas Day made Rory feel full of warmth and joy, surrounded by all the people she loved. She and her mother went up to her grandparents for a sumptuous, decadent Christmas brunch, attended by more than a few of her grandparents' closest friends from the club. Her grandfather passed her an envelope with a wink and a grin, and when she opened it she found tickets to Broadway's _Phantom of the Opera_. "Now we have a perfect excuse to visit you, Rory dear," Emily kissed her on the cheek, "February, box seats."

"Wow, thanks," she gave them each a hug, "it'll be so nice to have family visit the city for a minute."

They asked about her job and her apartment, but she shrugged off the questions, not in the mood to talk up her glamorous position as a glorified Starbucks delivery girl. In a year or two, when she got a promotion and could write her own things, she'd feel more comfortable talking about her job to her grandparents. For now, it was best to mention the name a lot ( _New York Magazine_!) and avoid the dirty daily details.

Rory spent the rest of the brunch doing her best not to laugh as her mother not-so-quietly impersonated various members of the club crowd. When it was time to leave she gave her grandparents one last hug and thanked them again for the tickets. They handed Lorelai an envelope too, with a check inside that made Lorelai swat Richard on the shoulder, "Dad, you didn't have to do that."

They had agreed to host Christmas dinner at their house, so they were quick to get home. Lorelai had snorted aloud at the idea of cooking anything, so Luke and Sookie had both promised to split the responsibility and bring a few things pot-luck style. Sookie and Jackson showed up in a whirlwind of heavy platters, stacks of Tupperware, and small children running about still high off of the joy of their present-filled morning. Luke showed up more subtly, arms laden with grocery bags and Jess behind him holding a case of beer.

"It's not for me," Jess assured Rory, setting it on the porch out in the cold. "think I would drink this domestic crap? Come on. Luke said he knows what Jackson likes."

"They do all like that," Rory shrugged, and helped him grab a few for the adults that were running the kitchen.

The afternoon quickly darkened into evening, and soon enough the table was stacked tall with a perfectly delicious collection of Luke and Sookie's finest. It was a small, cozy group dinner, and Rory spent the meal gossiping with her mother and Sookie as the kids entertained with their sugar-high antics. She tried to help with the dishes but Luke shooed her away, handed her a half-empty wine bottle and told her to go relax with her mother.

In the living room the kids played games until they crashed, while the adults hung around, finished the case of beer, and talked about old times. The twinkling lights on the tree and the marathon of Christmas movies on ABC helped to soften the tone of the evening, everyone wrapped in blankets and sleepy-full on too much amazing food.

Rory eventually noticed that Jess had pulled out Hemingway and was reading in the corner chair. He had one foot balanced on his knee, a short glass of either whiskey or scotch resting on the armrest. The kids laying on their stomachs and playing a game by his feet didn't seem to phase him in the slightest. His eyebrows were furrowed, concentrated, one hand casually flicking through the pages as he absorbed the text.

Eventually Sookie's family left, and Rory found herself on the couch with Luke and Lorelai watching an old Christmas flick. A phone buzzed, and the three of them glanced over at Jess.

"Hey! Silence during the movie!" Lorelai shushed him.

He held up one hand in defense and answered the phone, quickly putting his book and glass on the side table. "Hello? Hey, Em."

He moved into the kitchen, listening to whoever was on the other line. "Em?" Lorelai raised her eyebrows at Luke, grinning.

"Some new girl, Emma," Luke shrugged, "he told me she works at the bar down the street from the publishing house or something. I don't know, he doesn't talk much."

Rory sipped her wine. She felt more or less unsurprised. There was no way that Jess, with his dark eyes and bad-boy charisma, stayed single for any length of time. But the comfort in the way that he answered the phone and the easy manner in which he shortened her name did surprise her a little. He was clearly relaxed with her, whoever this Philadelphia girl was.

She tried to shake Jess out of her head, focusing on the TV and the wine. Of course he had a girlfriend.

Late in the evening, after Lorelai and Luke had headed upstairs, Rory stretched out on the couch. Her mind was hazy with wine and food. She could feel the pressure of her work emails beginning to close in on her, but she pushed it away, refusing to think about it until she was back on the train to New York the next morning.

"More whiskey?" she offered Jess, reaching for the bottle on the coffee table.

He reached from his chair to hand her his glass. "Thanks."

He took a swig, and rubbed his eyes, tired. After a long pause he rested his head back against the chair and closed his eyes. "My editor is going to be so pissed at me."

"Why?" Rory poured herself a glass too. Her head was heady and she wanted to keep the buzz, enjoying that capricious and pleasurable halfway place somewhere on the road between sober and dizzy.

"She wanted my next draft by the new year," Jess said, "She liked the first one but wanted a rewrite of the ending."

"Endings are hard," Rory sympathized.

"The first one was shit," Jess stared at his glass, "I knew it. Sent it to her anyways."

Rory watched him, patient. He sighed. "Oh well. Age old cliché story. Writer hitting a block."

"What's the story about?" she asked, curious.

Jess sipped his whiskey, his voice heavy with self-deprecation. "Nothing like _Subsect_. Something of a love story I suppose but the characters are too messed up to realize it. Set in New York, like every other novel."

"Sounds like a success already," she smiled, "I'm sure I'll be seeing it on the New York Times bestseller list – they love the ones set in New York even if they try to pretend they don't. Self-indulgent, all of them."

Jess nodded. "True. But last I checked most bestsellers had endings."

"That's true, they do tend to have endings."

Jess swirled his whiskey. "Maybe I'll just sell out, not resolve anything, and leave it at a cheap cliffhanger. I've heard authors consider that a noble option these days."

"Don't do that," Rory frowned, "you're better than that."

"My editor would disagree," he said darkly, "I've got a week to fix this before she starts offering me her own equally awful suggestions."

"My offer still stands, Mariano," Rory pulled her feet up on the couch, curling up against the arm rest. "If you need ferocity of editorship, you know where to look. I can give it a go."

He seemed hesitant, watching her, deliberating. "No one has read this other than my editor. It's an unfinished disaster with plot holes and inconsistencies and unrelatable, unlikable characters."

Rory scoffed, "You're a gifted writer, there is no way that it is that bad. Maybe it just needs a fresh set of eyes?"

"Maybe," he finished the rest of his glass in one swig, and half-stood to pour himself another. Without asking, her leaned toward her and topped her glass off as well. In his suddenly close proximity she caught a snatch of his cologne, a familiar, woody, whisky-aged something that reminded her of pine needles and the worn leather binding on old books. "My condition still stands as well, I would fully expect for you to shred the thing to pieces."

"Blitzkrieg of criticism," she raised her class to him.

He clinked his glass against hers, "I expect nothing less."

She smiled despite herself. He settled back in his chair, and caught her grin. "What?"

"I'm looking forward to reading it," she admitted. "Subsect was brilliant. You know me, I can't resist good literature."

"Lower your expectations," he warned.

"Sure," Rory held up a hand, but she couldn't quite suppress the smile pulling at the corners of her lips.

"Well," Jess drained his glass, "if that's the case then I suppose I should get you a copy before you head out. What time is your train?"

"I'm leaving at noon tomorrow."

"Great, pick up the copy at Luke's before you go? I'm driving back earlier than that."

Rory nodded, "Sounds good."

He stood, picked up his beat up paperback book and tucked it into his back pocket. She watched him put on his coat, his motions just a touch too slow, the whiskey making some kind of effect on his bloodstream.

"It was nice to see you," she said. She meant it.

Jess glanced up from his coat buttons and gave her his typical, crooked smile. "Nice to see you too. Kill my book, will you?"

"I'll send you the ashes in a few days," she promised.

"Alright." He walked past her, behind the couch, giving her shoulder a short squeeze as he passed by. Like a habit she reached up towards her shoulder, fingertips lightly touching the back of his hand, a brief moment of contact before he vanished towards the front door.

"See you," she twisted in her seat. Jess' dark eyes passed over her once, thoughtful, and then he opened the front door and disappeared into the dark, cold night, quickly shutting the door behind him to block out the icy rush of air.

She turned back around and stared at her whiskey glass, at the inch or so of dark, amber liquid that made her head spin and her thoughts fuzzy.

Perhaps she was an idiot for pushing her editorship on Jess, for pressing their friendship despite doing her best to pulverize it the last few times they had met up while she was at Yale. She felt herself unconsciously pulling the familiar strings of their connection again, pressing gentle conversation about literature and prose, offering whiskey and friendship when she knew that they were both disasters with each. But Jess was careful and guarded, sending book recommendations and giving witty one-liners without really letting her in. Maybe it was for the best, maybe he was protecting himself from the aching damage they had tended to inflict on each other in the past.

Or maybe she was being utterly narcissistic and Jess was still unbothered, careless, removed from whatever history they had once shared. He answered the phone with a smile to an Em in Philadelphia and kept a careful distance from Rory. Maybe all of this was in her head and when he walked home she wasn't on his mind at all. More than likely he was running over the plot of his book, trying to tie together an ending to an uncooperative narrative. Or maybe – and she took too large a sip of her whiskey and winced at the rush – he was imagining a girl in a dark bar in Philadelphia with her own bottle of liquor and her own strings to pull.

Rory stretched out and lay back, closing her eyes, pushing her thoughts away from the closed off ex-boyfriend that had left her living room feeling remarkably empty. In the morning she would wake up to pots of coffee, a heaping breakfast at Luke's, and a thick sheaf of papers in a manila envelope with Jess' name and characters. She would have literature to read and creative, constructive criticism to contribute. For the first time in months, ever since becoming a glorified intern, she would have real, valuable writing to peruse and explore.

Her inner editor smiled.

* * *

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 **Reviews are always, always wonderful.**

 **And (shameless plug) for those of you wishing for a different imagining of the Revival, check out _Fall is for Funerals and Vonnegut_ :)**


	3. Chapter 3: Summer 2009

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 **Chapter 3**

 **Summer 2009**

Jess drove into Stars Hollow with the windows rolled down, his left hand lazily coasting outside, catching the warm July breeze as it flew by. He kept his foot firm on the gas pedal though, his perfect, consistent five-over-the-speed-limit betraying his urgency. Lorelai, in full-meltdown mode, had made the accident sound terrible over the phone, but Jess knew the woman better after a decade of drama. Had Luke been seriously hurt – _truly_ life-threatened – she wouldn't have included the barrage of near-hysteric jokes and pop culture references and some long-winded anecdote about how Luke would inevitably fall to the drug epidemic if he ever managed to recover from the amputation and battlefield infection.

He pushed the speed a little faster. It was dangerous waters to speed in the land of Taylor Doose, but today it was worth the risk.

The town was in full summer mode, nearly bursting with American flags and tourists enchanted by the cutesy shops and eccentric townspeople. The trees were full and leafy, and the air smelled like some Hallmark-perfect summer mixture of flowers and Kirk's hot dog stand. Jess weaved his way through all of it, parked in front of the diner, and left his keys in the ignition.

The diner was locked, a firm CLOSED sign on the front door with a sticky note that looked like Lorelai's handwriting that read GONE FISHIN' FOR MEDICAL ASSISTANCE _._

Jess shook his head, unlocked the door, and quickly went upstairs to the apartment, taking the steps two at a time. If he remembered correctly, Luke kept his insurance card with all the other important documents that he deemed useless in a drawer by the refrigerator. Luke had never taken the whole insurance card thing seriously, a by-product of not needing it for a good fifteen years running.

He dumped the contents of the drawer on the kitchen table, and flipped through the stack of papers. Finally, he found the small laminated insurance card wedged between what looked like the title to his truck and an old Luke's Diner takeout menu. He tucked it in the back pocket of his jeans and hurried back down the stairs.

The hospital wasn't too far away from Stars Hollow, and Jess drove fast once he got out of the small-town tourist nightmare. When he pulled into the parking lot he saw Lorelai's jeep parked haphazardly across two spaces, one of which definitely said reserved for handicapped. Jess rolled his eyes and made a mental note to steal her keys and move her car before she got a ticket, or worse towed.

The woman at the front desk looked up when he entered, and he caught the familiar shift in judgment that was written all over her face. He wasn't looking his best, if he admitted it. He had been on a writing binge when Lorelai called; his clothes were wrinkled, he had heavy bags under his eyes after a couple days without sleep, and he hadn't shaved. He was in full on scruffy artist in black jeans and a Bob Dylan t-shirt mode, and he knew any normal receptionist would think he was up to no damn good.

"Here to see Luke Danes," he said. He tossed the insurance card on the counter. "I guess you needed his insurance card before you started treatment."

"Ah, yes, Mr. Danes," the receptionist took the card gingerly from the top of the counter, "Thank you, I'll put it in the system and let the doctors know."

"Great. Where is he?"

"You're not allowed to see him unless you're family," she said, her eyes on the computer monitor as she typed.

"I'm his nephew."

She paused and warily looked him up and down again. "Name?"

"Jess Mariano. Where's Lorelai Gilmore then? His …girlfriend?"

"We wanted to give her a sedative for hysteria, but apparently my medical recommendations don't have value without the power of the prescription pad," the receptionist said sourly, "she was in here up until a few minutes ago, I have no idea where she ran off to."

"You shouldn't leave her unattended," Jess shook his head.

"Yes, well, at least she isn't in here," the receptionist checked something on a pad of paper by her elbow, "Unfortunately you really can't see Mr. Danes, they're going to bring him in for surgery now."

"Great," Jess ran a hand through his hair. "How long is that going to take?"

"They're going to need to reset the bone, probably insert a screw or two. I'm not sure," she swiveled her chair away from him, "go sit and wait."

Jess pushed off from the counter, irritated. The waiting room was nearly empty save for a nervous looking young man that was flipping through a tattered copy of _What to Expect When You're Expecting_ and an elderly woman that was knitting something that looked suspiciously like a dog sweater. He scanned the signs, and saw an arrow pointing towards the cafeteria.

Unsurprisingly, he found Lorelai by the coffee machine, fighting with a stack of Styrofoam cups that were stuck together and muttering curses. "Goddamn … stupid … give me one, you monsters …"

"Need help?" Jess leaned against the wall, folding his arms.

She spun around, and looked immediately relieved. "Jess, thank god you made it. You got his insurance card?"

"Yeah, they have it, they're taking him in for treatment now," Jess held a hand out for the cups.

She handed the stack to him. He unstuck the top cup by unscrewing it like a jar top, and then popped a second cup off for himself. Lorelai filled them both to the brim with hot, dark coffee, mercilessly draining the machine.

"Thanks Jess," she tossed the still-stuck stack of cups carelessly into the corner and handed him his coffee, "you're a real hero today."

"What happened?" he asked. He held his coffee with both hands.

"It's my fault," Lorelai's eyes became a little teary. She bit her lip, eyebrows drawing together. "I threw Paul Anka's toy and it got up on the roof, so I asked him to grab the ladder and get it – Paul Anka gets _very_ cranky when he loses his toys – and he was already late for the diner and he didn't really have time so he rushed and didn't prop the ladder up right and the gutter – which he's been telling me to get replaced for _years_ – broke under the pressure and Luke, the toy, the gutter, and the ladder all fell onto the ground and he was knocked out for a few minutes and you should have _seen_ his leg, all broken and sticking out funny, and I had to get the ladder off of him and he was bleeding in my car and in so much pain and then we got him here and that damn idiot woman at the front desk and the doctors _refused_ to help him until we got the stupid insurance card. I swear. And I locked the keys to the diner inside the diner and we would have been absolutely screwed without you."

"It's no problem. I was at a friend's apartment in New York anyways, I was only an hour or so away." Jess frowned, "Seems really unlike Luke to not set the ladder up right."

"I know," Lorelai said miserably, "he would have been okay but the gutter was falling apart and he forgot about the cracks in it."

Something still wasn't quite adding up for Jess, but he didn't want to push her. Luke wouldn't have forgotten about the weak gutter unless he had something else on his mind, and Jess knew that being worried about being late for the diner wasn't enough for his uncle to forget about the structural integrity of a building.

Lorelai rummaged through the cabinets and found a giant bag of ground coffee and a stack of coffee grinds. Without hesitating, she dumped the existing grinds into the trash and began fixing a new pot.

"Paul Anka … I have to call Babette, tell her to check on him. Did you re-lock the diner? I don't want Kirk in there."

"It's locked," Jess sipped his coffee, wrinkling his nose at the harsh bitter taste. "Hospital coffee is the worst."

"But at least there is coffee," Lorelai said darkly. She finished the pot and hit brew, distracted. "I have to call Michel too, tell him not to kick everyone out just because I'm gone. And Sookie, she'll be worried…" She paused her train of thought and looked at him, "A friend in New York? Who were you with?"

"Emma has a friend who lives in Astoria, but she's been out of town for a few weeks. Told me I could use the apartment for writing, as a get away." Jess said.

"What, you can't write in Philadelphia?"

"I write better in New York," he said.

It was true, there was something about being in the city, in his old neighborhoods, about finding niches in coffee shops and bars in the dark literary underground of the Village that still reeked of Dylan, Kerouac, and Ginsburg. Jess could write in Philadelphia, at his messy desk above the publishing house or in one of the many bars he frequented as excuses to anesthetize writer's block. But, when he needed to get serious, needed to put words on paper and pen the narrative lurking in the back of his mind, he went back to where he grew up. New York was a writer's paradise, the traffic and the crowds barely camouflaging the throbbing heartbeat of literature and poetry that ached beneath the concrete and steel bones of the city.

"You artists," Lorelai shook her head. "I'm going to make a few calls – when this is finished could you just take the whole pot and meet me in the waiting room?"

"Sure," Jess said, amused.

She disappeared down the hallway, phone in one hand and coffee in the other. Jess waited for the coffee, drumming his fingers on the counter, lost in thought.

He was worried about Luke, certainly, but the broken leg and whatever other physical damage was caused by falling off of a ladder wasn't what was bothering him. Luke would never be that absentminded, not unless something was seriously on his mind.

Jess would hazard a guess that something wasn't quite right between his uncle and Lorelai, but he wouldn't know until he saw Luke. Lorelai was too much of a mystery to him. She had an unnerving way about her that hid the reality of her emotions beneath layers and layers of snark, humor, rambling, and denial. Jess was good at reading complex people, but he didn't have the time or patience to try to unpeel Lorelai Gilmore. Usually, whenever he saw her when he visited Luke, he verbally sparred with her through sarcasm and cultural references and stayed the hell away from anything resembling an honest conversation. They both liked it better that way, keeping their respectful distance through wit and banter.

He knew that she would probably never feel entirely comfortable around him, not after his ill-fated senior year in Stars Hollow and the way his teenaged self had thrown her and her daughter's lives into an uproar. He didn't feel that comfortable around her either, if he was honest with himself. She kept him at an arm's length distance away, warm and bubbly and funny and just a touch removed.

The coffee finished brewing. Jess did as he was asked, grabbed the handle of the pot, and made his way back into the waiting room. The receptionist shot him a look, but he ignored her, set the pot on the table near Lorelai, and sank into a seat a couple spaces over.

He pulled a notebook and pen out of his bag and tried to get back into the torrent of writing he had been in before his phone rang that morning. He read a few pages but his eyes kept re-reading the same lines over and over, his gaze unfocused, catching moments of Lorelai's rapid fire conversations and turning the day over in his mind.

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* * *

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A few hours later, after Jess was thoroughly sore from sitting in the hard hospital chair, the receptionist finally told them that they could go in to see Luke. Jess hadn't moved except to move Lorelai's car, so his joints were sore and his head was beginning to pound from the fluorescent hospital light. He followed Lorelai – who nearly ran after the nurse – down the hallway and into Luke's room.

Luke looked terrible. He had a large purple lump rising from his right temple, and a gash across his cheekbone. His leg was in a cast and propped up, and he had a variety of tubes running from his arm to an IV machine. He looked at them groggily through one eye.

"Luke!" Lorelai's hands fluttered, unsure where she could touch him that wouldn't hurt, "are you okay? How do you feel? You kept the leg? Interesting choice."

"I'm fine," Luke's voice was raspy, but had his usual gruffness, "leg hurts. Nothing serious."

Lorelai settled for patting his right hand, which looked more or less unbruised. "I am so sorry Luke, and I know Paul Anka is sorry too. I can't believe it broke like that!"

"Well, I was an idiot for not picking a different spot," Luke saw Jess by the door, "hey, what are you doing here? I'm not on my death bed, it's just a broken leg."

"Had to get your insurance card," Jess said. "You look like shit."

"Hey!" Lorelai shot him a look.

The corners of Luke's mouth rose, "Yeah I bet. You sticking around today? Doc says I can go home as soon as the IV bag is done."

"Really? They're not keeping you overnight? You can come home today?" Lorelai seemed relieved, "the woman at the front made it sound like you'd be trapped here for weeks and I would be banned from the property and never see you again."

"I can go home soon," Luke grimaced, "but I'm going to be in this cast for a while. The doctor said I get a wheelchair, can you believe him? I can't run the diner in a wheelchair!"

"Cesar can run the diner," Lorelai said dismissively.

Luke snorted, "Yeah we'll see."

Jess helped fill out Luke's paperwork and stayed out of the way, tucked in a chair in the back of the room, until the doctor came in and finally cleared Luke for release. Jess overheard the pain medicine prescription and raised his eyebrows. Luke was going to be flying high for a good couple days.

It was probably a good idea to hang around for a little while, Jess decided. He trusted Lorelai to keep Luke alive, more or less, but something told him that they needed help right now. While the doctor and Lorelai packaged Luke into the wheelchair, Jess stepped outside and gave Emma a quick call. She didn't pick up, so he left her a short message explaining what had happened and promising to be back in Philly by the next weekend. He wasn't worried; Emma never minded when he disappeared to Connecticut to be with Luke.

Jess drove back to Stars Hollow behind Lorelai's jeep, and helped unload Luke from the jeep and half-carry him up the short steps and into the house. There was no way to get him all the way upstairs to their bedroom, so Lorelai quickly grabbed what looked like every pillow and blanket in the house and made up a makeshift bed on the couch. Jess helped him lay down and carefully propped his uncle's leg up on the armrest.

Paul Anka came up and rested his head on Luke's chest with big, mournful eyes. Jess snorted.

He went into the kitchen and checked the refrigerator. To his partial surprise it was practically empty, with only a few beers and condiments. It wasn't like Luke to have an empty kitchen.

Jess' head was beginning to get a bit full of mental notes to ask his uncle about, but he kept his silence, grabbed his keys, and headed to the grocery store. Maybe it was too much to expect Lorelai to keep them both alive until Luke was mobile again.

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* * *

.

Jess stayed in Stars Hollow for the next handful of days, camping out first in the big armchair in the living room with Luke and then, when he was sure Luke wasn't going to try to get up and do things in the middle of the night, back in the old apartment above the diner. Lorelai had approximately a dozen crises to deal with at the Inn – a kitchen fire, a broken washer, a fired maid – so she was gone for most of the days, a whirlwind of smart business casual attire, snappy tired phone conversations with Michel, and frequent stress eating. Jess watched her hide the poptarts in Rory's old room to avoid causing Luke undue stress. Now that they were out of the hospital, and Jess observed her for a few days, he could begin to see that something was wrong with Lorelai.

Luke quickly became impatient with both the drugs and the couch, and it became a fulltime job for Jess to keep him immobile and medicated. Luke called Cesar roughly every thirty minutes to ask about the diner, and shouted instructions over the phone. "Did you rewire the toaster? Remember, if it's plugged in, you have to temporarily turn off the blender. How are the groceries? Do you need me to go buy eggs? We always run out of eggs. What about coffee? How's the coffee? New pot every hour and a half?"

Jess let him go on for a few minutes before prying the phone away, apologizing to Cesar, and hanging up. Luke would try to stand up, and then quickly collapse backwards, swearing, wincing at the agony of his leg.

"Take your drugs," Jess said, rolling his eyes.

"No, they make me feel woozy," Luke gritted his teeth, trying to put his leg back up on the armrest.

Jess stood up and helped him re-prop his leg. "Take the drugs! Look at you, you're miserable."

"I'm fine!" Luke insisted. But his face was white and when Jess handed him a glass of water and the pills, he took them after only a handful of muttered comments.

Lorelai brought in take out every night. She sat on the floor and leaned on the couch by Luke, turning on marathons of his favorite movies or, even more surprisingly, sports games. Jess ran errands or did the dishes, catching brief observations of them. After two days, he was sure that something was wrong with Lorelai. Her cheerfulness seemed hollow, as if she was prattling jokes and witticisms on autopilot. Luke would reach down and hold her hand, careful and comforting, but she seemed to hardly notice him.

On Thursday night, when the football game was on and Jess was sitting by Luke in the otherwise empty house, he asked about it. "Something up with Lorelai?"

"Huh?" Luke glanced over at him, then refocused on the game. "No, nothing's up, why? Having a bad week at work it sounds like."

"You sure?" Jess was patient. He sipped his beer. "She seems off."

"Off?"

"Yeah, like something's wrong."

"Nothing's wrong," Luke said.

"What was on your mind the other day?"

"On my mind? What day?"

"The day of your accident," Jess said, keeping his voice light. "Why'd you fuck up the ladder? What was on your mind?"

"Nothing was on my mind," Luke said, "I just made a dumb mistake."

"Something was on your mind," Jess countered.

Luke was quiet for a second. "Hey, can I have a beer yet?"

"No, you're not mixing pain meds and alcohol," Jess tipped his beer toward him, "but I get one since I have to deal with you."

Luke shot him a look, exasperated.

"So what was on your mind?" Jess persisted. "I've seen you when you're distracted. You tried to pour dishwashing fluid in a coffee cup and serve it to a customer. You forgot where the menus were. You called Kirk 'Kurt.'"

"I did that one on purpose," Luke disagreed, "it drives him crazy."

"Fair enough," Jess smirked. He waited.

After a few moments, Luke sighed. "Look, Lorelai's just having a rough month. And when she gets stressed she gets a little manic. And you know I want to help her out but I don't know how."

"What's wrong with her?"

"Ah, she had a bad fight with her mom," Luke said, "and she's not doing too well with Rory either. I swear, when those two are fighting, it's like the whole world turns inside out. Mercury in retrograde and all that crap."

"Rory?" Jess raised his eyebrows, "what are they fighting about?"

"Something about the job in New York, I think? I don't ask. It's their business, they'll figure it out. They always do."

Jess nodded, and then returned his attention to the game and allowed the subject to drop. Luke swore when the other team scored, and Jess cracked a smile. If he was lucid enough to pay attention to football, then he was getting better.

.

* * *

.

Late that night, after Lorelai came home, kicked off her shoes, and dozed off on the floor by the couch, Jess returned to the apartment above the diner. He sat on his bed, back resting against the headboard, and popped the lid off of another beer. He reached for his beat up messenger bag and pulled out a stuffed manila envelope, his laptop, a notebook, and a pen.

He flipped the envelope over, unhooked it, and pulled out a familiar sheaf of paper. The manuscript itself had been approved by the editor months ago, and was already in the queue for being printed, bound, and distributed to stores in late August. But he kept this old copy with Rory's scribbles on it because something in the delicate, careful way she opened the lines of his writing, fingers and thoughts catching on the strings of plot and prose, made him re-evaluate his artistry and re-align his thoughts for his current project.

She had sent him back the manuscript only a few days after he had seen her at Christmas. It arrived at the publishing house in Truncheon with his name printed in her familiar handwriting. He had been a little surprised at the speed of her edit – had she even read the damn thing or did she think it was bad enough that it should be scrapped entirely? But when he opened the envelope and began flipping through the pages he saw her narrow handwriting on nearly every page, an interwoven web of delicately worded questions, quotes that she rewrote merely because she loved them, individual word suggestions, and the rarest of circled punctuation marks. She underlined phrases that, in her words, were so good that they made her bitter that she had not come up with them first. She unraveled characters, listing out their development in a neat, bullet-pointed way that made unresolved arcs obvious and shoddy consistency apparent. She looped faint question marks by paragraphs that he knew were unclear but hadn't had the motivation to fix anyway, and gave him gentle exclamation marks at the parts that heaved with torrents of emotion and passion.

In Philadelphia, at his disaster of a desk with a half-empty bottle of whiskey, he lost himself in the pages of his own work and the dialogue that existed between his typed letters and the lines of her penned cursive that crisscrossed the pages. The cold December hours passed from late afternoon to early morning, and he found himself, pen in hand, editing alongside her, scribbling answers to her questions, re-writing passages that she questioned, defending one character and destroying the next. When he reached the end – that messy, incomplete, unsatisfying disaster of an ending – he found a near essay of cramped writing. Her writing began to slant, hurried, rushing across the page, bumping into the lines, swelling with the dozens of thoughts that she put on paper about the conclusion of his narrative.

She concluded what was practically a persuasive essay with a neat, simple, rhetorical question. "Isn't there something beautiful in them never finding one another again?"

He read the line once, twice. He poured himself a shot of whiskey. He had fought with these two characters, a drug addicted poet and an alcoholic musician, two artists too self-absorbed to give their love story the attention it deserved, too narcissistic to allow a romance to live, or god forbid, let themselves find happiness. He knew they would not have a happy ending (his characters, he was realizing, never really did), but he was trying too hard to give them _any_ ending, any closure, a brawl in a seedy dive bar at three in the morning, a clipped one-sided phone call, a letter posted from an anonymous mail box, an unexpected meeting years later after they each succumbed to adulthood or suburbia or parenthood or god knows what.

Perhaps this was how they ended. Perhaps they never _did_ end, and that was the soul-crushing, inconclusive, painful beauty of it all.

He set pen to paper and rewrote the ending in an hour. It flowed out of him; his words felt like thorny vines growing in fast-motion to weave together and create an impenetrable hedge, a barrier, a firm end to a story that needed to end and never end all at the same time.

When he was finished two days later with the edit that broke the dam, he spent the money to reprint the manuscript twice, once for his editor and once for Rory. He sent it to her with a note: _There's nothing to writing. All you do is sit at a typewriter and bleed,_ he quoted Hemingway. _Thank you for making me bleed. - J_

It was only days after he sent it that he realized, with their history, she could misconstrue what he meant by bleeding. But he shrugged it away. She had ripped the prose right out of him, and he was grateful to her for it.

Here, in the apartment of Luke's diner, he let his eyes scan her edits once again, reading through her questions and assumptions, her comments and her quotes. It felt like a familiar conversation with an old friend. He had memorized the words and the sentences, allowing them to motivate him to push further, to demand more of his writing, to elevate his craft.

He set his pen to his notebook and continued his chapter, occasionally glancing back to the cursive words on the typed pages of his old manuscript.

.

* * *

.

Finally, when Luke was off his meds and able to begin to hobble about using a pathetic combination of crutches, hopping, and cursing, Jess felt like he could get back to Truncheon and continue working on his book. He restocked the fridge one last time, made sure the ladder was locked in the garage with the key hidden away, and told Luke to call him if he needed anything.

"Thanks a lot Jess," Luke said, "I, you know, I really appreciate you coming here and helping out with the house and Lorelai and everything."

"Anytime," Jess said. He meant it. He picked up his bag. "Don't get up, stay on the couch," he warned, and clapped his uncle on the shoulder. "Cesar is going to call me if you try to come into the diner at all in the next three weeks. You're banned."

Luke rolled his eyes. "Great. Can't even run my own damn business."

"Nope, not until you can walk there," Jess pulled out his wallet and handed Luke his insurance card, "here, almost forgot."

"Thanks," Luke flicked it onto the side table.

Jess gave him one last one-armed hug, and then headed to the door. His car was at the diner still. When he opened the door he saw Lorelai sitting on the stairs, talking on the phone, her head in her hands.

"I think you're making a big, big mistake …. Rory, that's how the world works. We get jobs, we stick it out through the early years, we get promoted, the jobs get better. You have to put in the time …. No …. No, Rory, come on, that's not fair … what are you going to do? How are you going to pay rent? … well if you were my normal, responsible kid I would have, I don't know, assumed you'd gotten another job or something lined up first … no …"

Jess felt stuck, awkward. He opened the screen door and Lorelai glanced back at him. He passed her, heading down the stairs, but she tugged on his jeans and mouthed for him to wait a second.

"Look, Rory, you do what you want to do. It's just hard for me to watch you give up on your potential dream job over a couple months of entry-level work … yeah … well, let me know your plan I guess … of course I want you to be happy – I want the best for you! That's why I don't understand why you're quitting … okay … okay, bye."

She hung up the phone and took a deep breath, her eyes closed, and exhaled. "Sorry about that, Jess."

"Everything okay?"

"Yeah," Lorelai stood up, brushing off the conversation, "listen, it's meant the world to Luke to have you here the last week. Thank you so much. I mean, I can hardly feed myself, let alone Paul Anka and a grown man that won't eat poptarts. You've been a lifesaver."

"No problem, anytime," Jess shrugged, "I still owe him a lot, so consider it partial debt repayment."

Lorelai smiled. She looked tired. "See you around the holidays?"

"Probably," Jess said, "one or the other. I'll let Luke know."

"Great," she stepped backwards and blew him a quick kiss, "bye Jess."

He nodded, and then turned and walked back to the diner, thinking about the phone conversation that he had overheard.

The drive back to Philly was long, as always, and snarled with traffic around New York. Jess listened to some of his favorite old punk bands and let the week sink into him. His thoughts flitted from the notebook in his bag to his uncle to Lorelai sitting on the porch, pleading with her daughter not to quit her job.

He parked on the street. Before he walked inside, he pulled a piece of paper out of his bag and an envelope.

He scrawled his phone number on the paper and added a quick note.

 _If ever you need whiskey and sympathy. – J_

Without hesitating, he wrote her New York address on the envelope and sealed it. He threw his bag over his shoulder, locked his car, and, quickly and casually, slipped the envelope into the post box on the street before heading up the steps to the publishing house.

.

* * *

 **Always grateful for reviews - Thank you to everyone who has given me feedback and support for this so far, and thank you to those who read _Fall is for Funerals and Vonnegut_ :) **


	4. Chapter 4: New Years Eve, 2009

.

 **Chapter 4**

 **New Years Eve, 2009**

Rory slammed the door to her favorite Brooklyn coffee shop a little too hard behind her, trying to block out the icy wind that caused goose bumps on her legs through three layers of leggings and jeans. The crash jarred the tiny, empty shop, and the male barista threw her a haughty glance. She sighed as she approached the counter.

"Happy end of the year." The barista didn't even bother to look at her as he swept coffee grinds off of the counter. "What do you want?"

"Coffee. Large."

"Room for cream?"

"God, no." Rory, struggling with frozen fingers, pulled her wallet out of her purse and handed him a five.

He gave her change and looked pointedly at the tip jar. Rory, disliking his judgment, dropped part of it in the jar but pocketed the rest. She picked up her mug of coffee and went to her usual rickety table by the window.

The glass was frosted, hazy from the snowflakes that whipped the glass and stayed there, frozen. Rory wrapped her fingers around the hot mug of coffee and willed the heat to warm her numb skin. It was only a five minute walk from her apartment, but the day was a brutal, icy snowstorm.

Her book was in her bag ( _The Grapes of Wrath_ , because maybe the Dust Bowl could make her feel better about being stuck in the New York polar landscape) but she couldn't quite wrestle it out until her fingers regained feeling. She sipped the black coffee, relishing the heat and the bitter, dark roast.

She felt the urge to check her phone, but knew that it would include about a dozen missed text messages from her mother and probably a few from her grandmother as well, the digital vestiges of a blow up fight that Rory knew was coming and yet still could not believe had finally happened in the late hours of last night. She felt like crap after yelling at her mother, violently hanging up, and crying herself to sleep, but it wasn't shell-shock, rather more of a long-expected, tension-building nausea that twisted around her rib cage and made her want to throw up in her coffee.

When she quit her job over the summer her mother had been disappointed. Rory knew she would be, but she also could no longer bring herself to be a glorified coffee runner and photocopier. She knew she was meant for more than that, and even though her mother and her grandparents promised her that the grunt work would end and that one day she would be editing articles of her own, she felt like she was wasting valuable hours of her youth and her talents. It didn't make sense – Austen did not wait until she was old and withered to begin writing, but rather started as a child and continued through her youth, building her craft and developing her talents and making pieces and progress towards her adult masterpieces. Rory was an adult who was neither nurturing her craft nor building her talents – she was great at carrying hot coffee across Tribeca without spilling the majority of it.

Funnily enough, it was Jess' manuscript that started her on this plunge towards unemployment. She did not blame him for her lack of income, but rather felt grateful to him for forcing her to feel what she should feel every day – that purity of enthusiasm and determination, of seeing a block of visionary writing in its unpolished entirety and giving it all of the love and attention and feedback it deserved. Rory had taken his manuscript and devoured it, clutching the pages into the late hours of the night, taking a personal day from work in order to continue to scribble next to the neat typeface, pausing only to make coffee and gulp it down, unable to tear her eyes or attention away from the riveting and devastating narrative that he wove so expertly in his dry, sensitive prose. If she was meant for editorship, Jess was meant for artistry. He tortured his characters, wringing out their hearts, and patched them up just enough to tear them to pieces again. His writing was simultaneously thoughtful and blunt, heartbreaking and bitter. When Rory finally reached the ending (which was a beautiful catastrophe but a true writing catastrophe nonetheless) she did not try to push it towards eucatastrophe, but rather gently led it towards that slamming disaster that it so needed. Instead of encouraging him to let his two messed up characters come together again, she gave him the permission to allow them to wither apart.

The heaving torrents of emotion that Rory felt when she held the manuscript in her two hands, after a bleary twenty hours straight of editing, sowed the seed of doubt in her mind about her job. Yes, it was New York Magazine. It was also everything she shouldn't be doing.

She let her mother wheedle her into staying through the spring and early summer, listening patiently to her words of health insurance and résumé experience and references. But when she saw the press release for Jess Mariano's new novel, heralding a young Hemingway, something in her snapped. In July, she gave her boss her two weeks notice and told Lorelai that not even a 401k could keep her tied to a job that prevented her from doing what she loved.

Fall came and went, and Rory quickly ran out of money. She met her grandparents for lunch and pleaded for help with her lease until she found another job, promising to pay them back every cent. Emily allowed it, with the condition that Rory find a true _career_ this time, something that she could invest herself into. When Rory promised she would find an editing position, Emily just sighed. "You had that already, dear. And it didn't work out."

Nothing Rory said could convince her mom or her grandparents that her job for New York Magazine was _not_ an editing job. She sent out résumés, went to interviews, and read books in the quiet of her apartment, restless, unhappy.

The spark for the long-awaited blow up with her mother arrived last week on Christmas Eve at her grandparents' house, when Richard accidentally made a reference to funding Rory's unemployment. Lorelai nearly shattered her glass, but managed to maintain her composure at Emily's immaculate dining room table among all of their high society friends and colleagues. Rory caught the earliest train to New York, and avoided her mother's phone calls until she had the courage and the stamina to deal with the blowback that she knew she deserved.

"They can't bail you out of something like this, Rory. You need to, I don't know, really _feel_ the consequences of your decisions. You need to lose your apartment, to move home, to figure things out. You can't continue to live this fantasy New York life and think that everything will turn out okay because it won't, kid, not without hard work and sacrifice and all of those things that you shouldn't have to deal with but you do because you chose to."

Rory tried to interrupt, but Lorelai was insistent. "Your grandparents will give you money until they are no longer here, and then give you whatever is left in a beautiful, gift-wrapped trust fund account, but that isn't the point, Rory. The point is that you are a strong, educated, successful young woman and you _have_ to make things work out for yourself. You have to be independent! I didn't raise you to live off of their money, to take advantage of people you love to try to become what you think you should be. You can become an editor without this, Rory. You can find the job you love and the career you want without this -"

In the dark hours of the cold December night, hating herself and feeling like a proper screw up, Rory hung up on her mom and allowed herself to cry and eat ice cream and watch bad reruns of terrible reality TV shows.

Now, sitting at her usual table in the cramped Brooklyn coffee shop, watching the flurries of the storm and finally feeling the warmth in her fingertips, Rory cringed at the memories of last night and pushed the snatches of conversation out of her mind. She reached into her bag for the familiar pages of Steinbeck, and dove into the lines of literature like her sanity depended on it.

The depressed narrative drew her in to the struggles of the Joad family and made her feel extra terrible about spending her grandparent's money on the overpriced coffee that she was currently sipping in a neighborhood that she had no economic right to live in. But, determined, she continued to gulp down her coffee and read as the Joads struggled toward California, toward that false paradise that awaited them.

 _How can we live without our lives? How will we know it's us without our past?_ Steinbeck asked, pointing the words quite deliberately towards Rory.

She sipped her coffee, reading and rereading the line, pondering.

As if she had remembered an important meeting, she reached for her phone and screwed up her vision in order to avoid reading the long list of text messages on her home screen. Quickly, she typed in her passcode, hit new text message, and typed 'J' as the recipient.

 _Are you in the city?_

Rory reread the message once after she wrote it, then hit send, put her phone next to her coffee, and tried to rebury herself in Steinbeck.

Her phone buzzed almost immediately. His reply was short. _Unfortunately, yes._

She thought briefly about asking why it was unfortunate that he should be in New York, since he loved this city, his home, more than nearly anything he knew, but she honestly didn't care much. She typed back. _Meet me later?_

This time he took longer to respond. Rory made it through nearly three pages of Steinbeck until her phone vibrated. She snatched it up and read the glowing screen.

 _Webster Hall. 8pm._

She read the message, and then put her phone back on the table. The nauseous tendrils wrapped around her rib cage pulsed.

.

* * *

.

Long after evening fell, and the streets of Brooklyn became black and icy, Rory left her apartment bundled in her warmest coat and hurried towards the subway, slipping on the treacherous sidewalks. It was New Years Eve and the subway was crowded with groups of friends, joyfully chattering on their way to wherever the end of their year would happen, with champagne toasts or fancy dinners or god knows what else. Rory avoided the groups of laughing young people, glimpses of gold and sequins beneath their typical New Yorker black pea coats, their high heels and dress shoes at odds with the icy pavement. She felt like an outcast among them, a charity case that did not deserve to be getting on a train to go to a New Years Eve party in the village.

The Q dropped her off at Union Square, and Rory pushed her way through the throngs of people enjoying the bitter Manhattan night. Briefly, she thought of the thousands of wretched people stuck in Times Square, but quickly shook her head and wound her way towards Fourth Avenue. Those people would get their "life experience" and promptly regret it in these subzero temperatures with no bathroom access.

Webster Hall was the typical East Village music venue, a dancy club frequented by NYU freshmen that wanted to drink underage (and couldn't) and older NYC residents that sought that grungy vibe so desperately held on to by all Village establishments. Sometimes it had concerts that Rory thought would be legitimately amazing. Sometimes it had club nights that looked awful.

She leaned against the stone wall, shivering, avoiding the long line of glitzy young people in their New Years Eve finest that were hoping to get in.

Rory lost focus, watching the crowds, feeling disconnected and disinterested in the New Years revelry around her. She had no feeling in her toes or her fingers, but found she didn't care much. She was out of her apartment, observing the madness of the city, listening to the shouts of laughter that echoed through the old, dark streets.

"Hey." Rory felt a squeeze on her arm and warm breath in her ear.

She turned her head, recognizing the familiar scent of pine trees and whiskey, and saw Jess looking distastefully at the line of people waiting to get into Webster Hall. "Thank god we're not going here," he said shortly, and pulled her away from the wall, briskly walking past the throng.

"Where are we going?" she asked, unperturbed by his sudden arrival and his pushiness.

"Another venue – it doesn't have a published name so there was no point in giving you the address. This is close enough."

Rory bit back an eye roll. Of course Jess would go to some nameless, grungy basement music venue, too hipster to have anything as reputable as a website or an address.

He shoved his hands in his pockets and picked up the pace, weaving around the crowds and heading east. Rory glanced at him sideways. His familiar profile seemed tense, withdrawn, as if he was clenching his fists in his pockets. She looked back to her shoes and focused on keeping up with him, shivering in the icy wind tunnels of the avenues.

Finally, he stopped at a building on First Avenue with boarded up windows. Like a regular, he stepped quickly down to a door set below street level and opened it for Rory, beckoning her in.

Rory stepped inside and was immediately overwhelmed by the sticky, heady smell of alcohol and the deep, throbbing, bone-shaking beats of something that was both electronic and punk. The place was low-ceilinged and packed with people that looked like a typical grunge crowd: hair dyed various bright colors and sporting inches of dark roots, ripped band t-shirts, tattoos that were meant to be both serious and satirical, various piercings, and layers upon layers of black clothing. Jess, in black skinny jeans, an old black leather jacket, and looking like he hadn't slept in about a month, fit in perfectly. Rory, who was wearing her black pea coat but had a slouchy and possibly coffee-stained gray work sweater underneath, felt out of place.

She felt Jess place a hand on the small of her back and steer her towards two empty low stools set by the window to the street. Wordlessly, she sat. He unzipped his jacket, threw it on the stool next to her, and disappeared into the crowd.

Without him, Rory felt like she could get her bearings. If she craned her neck she could see glimpses of the band, back against the far wall, illuminated by red and purple lights. The crowd ebbed and flowed, pushing towards and away from the small bar, getting rowdier the closer it got to the music. The space was quite small – smaller than a tennis court – but somehow it did not feel completely compressed by the crowd within it. Chatters of conversation were drowned out by the steady electronic beats.

Rory took off her coat and ran her fingers through her unwashed hair, wishing she had brought lipstick or something to match the vibe and the night better.

Jess reappeared holding two short glasses filled nearly to the brim with dark liquor. He handed her one, sat on the stool next to her, and chimed his glass against hers. "Cheers." He said flatly.

She drank, obligingly. The whiskey burned her throat and made her wince. She indicated the height of the pour. "Did you bribe the bartender?"

"He's a friend," Jess replied. He took another drink and watched the crowd.

Rory observed him carefully. He had bags under his eyes, and he looked both pale and slightly ill. His dark wavy hair was a bit of a mess, as though he hadn't bothered to get a trim in a couple months, or really comb it at all, and beneath the sweep of dark waves his eyes were dark and inscrutable. One of his shoes tapped insistently on the floor. He hunched his shoulders and held his glass with white knuckles, as though he were trying to break it.

She took a sip of her too-full drink and let it burn her. Maybe she wasn't the only person having a terrible New Years Eve.

"What happened?" She asked.

He shot her a glance. "You first. Why did you text me?"

She made a face. "It's a long, embarrassing story. I'm a failure. I'm fighting with my mom. This year should have ended months ago."

Jess appraised her. His dark eyes were still hard, fiery, as though he was fighting something internally even as he composed himself enough to have a conversation. "Sounds like you fucked up."

Rory choked on her whiskey. She couldn't disagree. She tipped her glass to him.

They had only been sitting together a few minutes, but already Jess' glass was empty and hers was nearly there. He disappeared into the crowd again.

Rory bit her lip and watched as the people around her swayed and moved, couples weaving their arms around each other, friends shouting conversations over the music, groups ebbing and flowing with the beat. Jess seemed like he was a mess. And she knew that she was a mess. Perhaps this was a bad idea.

He returned, this time with another too-full glass of whiskey and something lighter for her. She took it gratefully. She could drink whiskey, but she couldn't drink it like Jess could, like he was trying to kill himself. She sipped the beer and sighed, heavily.

"What happened?" She asked, again.

Jess swilled his whiskey thoughtfully, his face stony.

She waited, patiently. The music and the alcohol were beginning to make her head pound.

" _If two people love each other, there can be no happy end to it_ ," he quoted Hemingway.

With a jolt, Rory remembered the 'Em' in Jess' life, the woman who had been flitting around the corners of their interactions over the last year or two. She watched him with a renewed sense of understanding and empathy. "No happy ending for you then?"

He shrugged, staring out at the crowd. "She's been cheating on me for a month, took up with some idiot at her work. Claims she didn't mean for it to happen, I'm gone too much, writing in New York, whatever."

Rory felt her heart wince for him. She looked away, out towards the band. The beat of the music caused her glass to vibrate and her head to begin to pound.

They sat in temporary silence. Rory sank back into her thoughts, haphazardly turning Jess' sentences over in her mind and trying to avoid the echoing snippets of her mother's voice from their conversation last night. They were both a sight for sore eyes, her and Jess. She was drowning in the depths of her own disappointment and incompetence, and he was suffocating in a tender, bitter, furious rejection that Rory knew only all too well from her gut-wrenching experience with Logan.

"You've cheated on people before," Jess said, as if stating a fact.

Rory felt as if she had been punched in the gut. "Thanks. Yeah."

"Why?" He looked at her. His eyes were still guarded, still dark and angry, but somewhere in them Rory sensed the devastation that he was grappling with. It quelled the anger rising in her stomach.

"He cheated first, so I felt justified. I wanted to hurt him like he hurt me."

Jess nodded slowly, and sipped his whiskey. "Sounds like a healthy relationship."

"It had its moments," she sighed.

He leaned back, tapping his glass. After a moment he looked directly at her, "Sorry, didn't mean to be an asshole there."

She shrugged it off. "I've been cheated on too. I know the feeling. It sucks. I wouldn't blame you for much right now."

Jess emptied his glass. Feeling like it was her turn, Rory stood, tugged the glass out of his hand, and pushed her way through a crowd of chattering people towards the small bar. She reached the counter by squeezing around a couple, and set the glass on the scuffed bar-top.

"He needs another one of whatever this is," she said, nearly yelling over the volume of the music.

The bartender, who was wearing a bleach-stained black t-shirt and had two full sleeves of colorful tattoos, glanced up at her. "Who?"

"Angry James Dean in the corner over there," Rory gestured towards where her and Jess were sitting.

The bartender nodded and grabbed a bottle of dark liquor. He pulled a fresh glass from underneath the counter and filled it halfway. "He needs to slow down or he's going to do something stupid."

"He'll listen to you more than he'll listen to me," Rory said.

"Anything more for you?"

Rory glanced at her own half-empty glass. "Sure. Why not."

It was a bit trickier maneuvering through the crowd with two full glasses, but Rory managed it with a few apologies and some minor stumbling. When she wound her way around the last large group, she caught sight of Jess, sitting alone, eyes unfocused and staring at the floor. She paused. He had his elbows resting on his knees, feet tapping, hands gripped together. It was as if she could almost see the weight, the gravity, of the maelstrom of hurt happening in the tension of his shoulder blades. Her heart broke a little for him.

She handed him his glass and squeezed his shoulder, giving him a little Hemingway in return. " _Life isn't hard to manage when you've got nothing to lose_."

"True."

Rory crossed her legs and sipped her drink, beginning to feel the heady influence of the alcohol coursing through her veins, making her vision blurrier and her reactions slower. She welcomed the slow burn. Normally she did not like to feel drunk, to feel out of control, but tonight she was perfectly happy to use Jess' coping methods to forget the mess that she had made out of her professional and her personal life.

"Your turn," Jess cleared his throat, pivoting towards her. "Why did you text me? Why did you fuck up?"

It was so Jess, not to ask her how she messed up, but why. He was the only person she knew that had always given her that room, to acknowledge that Rory Gilmore was perfectly capable of screwing up and generally deserved the blame for doing so.

"I had a pretty massive fight with my mom last night. It's been long coming. I'm a disaster of an adult."

"Disaster?" He raised his eyebrows.

"I quit my job over the summer and haven't found another one yet. I asked my grandparents to help me out until I could get stable again, but its been months and they're still paying my rent. My mom didn't know that they were helping me."

"You're living off your grandparents? Again?"

Rory avoided his gaze. "I don't feel like I'm not trying hard enough – I'm applying every day, I'm searching for that next position. I've actually turned down a couple of jobs because they weren't what I want. I feel like I'm being a stupid idealist, searching for that life-calling, and I know I need to suck it up and just get something that pays the bills, but I already had that kind of soul-sucking job at the magazine and I felt like a bigger failure there, fetching coffee and making copies and doing all of those things that I know I shouldn't be -"

"Rory." Jess interrupted her. She paused, still avoiding his eye contact.

He spoke deliberately, "It's not a bad thing to want to find a job that speaks to you. Hell, I spend half my time as a broke artist, so I _get that_. The difference – what I think Lorelai is trying to say – is that most people do that searching and also work somewhere that pays the rent in the meantime."

His logic – her mother's logic – was clear. But Rory still could not explain why she wasn't doing that, why she didn't have a job as a waitress or something to pay the bills while she searched for her career.

"What do you want to be doing, anyway? Do you still want to be an editor?"

She nodded. "You'll hate this, but you actually inspired me to quit my job."

Jess snorted. "I'm glad my vagabond ways are an inspiration for your unemployment."

"No," she rolled her eyes, "not your Kerouac fantasies, your manuscript."

"Ah," he took a sip of his whiskey. "Right."

"I'm serious Jess," she looked at him, insistent, "I haven't felt anything like what it was like to be absorbed in that manuscript, to be so involved and invested in a work of literature. It was like breathing again, to tear through a narrative and ask questions and pose suggestions and give feedback. You're a gifted writer, and it felt like nothing else to be one of the first to read something that poetic and write a dialogue that I knew, or I guess hoped, that the author would read."

Jess cracked a half-smile. "It was a disaster. You're the one that turned it around."

"It was not a disaster," Rory shot him a look, "it was incredible, Jess."

"Yeah, well," he swilled his whiskey, looking into the glass, "I guess it is poetic, or prophetic. Who knew I was looking into the future when I wrote that."

"You're not your character, Jess," Rory said softly.

He shrugged. "So you read my manuscript, felt something resembling passion about your work, and quit your job that would have eventually led you to that exact editing career that you realized you wanted?"

"But it wasn't that career," Rory shook her head, "it wasn't going anywhere. And even if one day I did become a senior editor, after developing all of my coffee-fetching skills, I wouldn't have been editing the kind of literature that I want to. Short stories and articles and interviews? I'm interested in _your_ kind of editing, Jess, that great literature, high artistry, grasping, aching kind of editing. I've spent my whole life reading every great book I could get my hands on – I want to continue doing that, to dive into that process and work with authors and influence those novels."

Jess tilted his head. "I guess it does seem much more _you_ to be on the book side of things, rather than the monthly publication side."

Rory sighed, collapsing back into her seat. "I'm not sure what that looks like, or how the hell I'm going to get paid, but I know now what I should be doing. And I'm just not willing to compromise."

The loud, steady beats of the music filled in the pause in their conversation. Jess finished his third glass, and weighed his words, unflinching. "I'd say not compromising on your life purpose is fine. It's compromising on taking responsibility for your livelihood, for your _rent_ , that is the problem."

His words were harsh. Rory flinched, and shot him an angry look. She took a large swallow of her drink.

Jess watched her, then stood. "I'll be right back." He disappeared into the crowd.

Rory nursed her drink and tried to ignore both her mother's and now Jess' words that floated through her mind. She felt both ridiculous and inebriated. Jess had offered her whiskey and sympathy, in that note months before, and she had taken him up on it with an inconsistent stream of back-and-forth texts, exchanges of literary quotes, music recommendations, and book reviews. But Jess never really was one for sympathy. If she sent him a quote referencing her self-isolation in Brooklyn, he responded with Virginia Woolf's plaintive stream-of-consciousness. If she sent him a music recommendation that could have betrayed her sense of personal tragedy, he responded with something that reeked of sarcasm and teenage angst. Tonight, he gave her whiskey, but he was not sympathetic to her story. In typical Jess fashion, he preferred to tell her how the world actually was, not how she wanted it to be.

He returned, stumbling ever so slightly on an uneven floorboard, and shrugged on his leather jacket. Beneath his composed exterior, Rory could begin to tell that he was drinking too much too fast. He held another glass of dark liquor in his hand. It was steady, but if Rory really focused, she could see a slight tremble in his grip.

"A new band is about to start," he told her, "they're better – we might actually want to listen to them."

"Great," Rory said. She meant it. Talking wasn't doing her any good.

He offered her his hand and pulled her up to standing. She followed him through the crowd, closer to the dimly lit stage. He found a small spot by the wall to lean against, and watched the new group check their amps and connections with blank, unfocused eyes.

Rory felt her normal, responsible self suddenly reappear. "Where are you staying right now? How are you getting home?"

"With a friend," he replied. "Walking distance."

"How far is walking distance?" she asked.

He rolled his eyes, "4th and Avenue A."

Rory sipped her drink, satisfied. It was only a couple blocks. Jess would be able to get there, even in the icy storm.

He gestured towards the bartender, and before she knew it Rory was holding yet another drink in her hand. "You're not taking the night seriously," Jess warned her.

"Seriously? What do you mean seriously?"

"I mean that clearly, Rory Gilmore, you and I have both royally ruined 2009. And if I have any say in the matter, I'd really like to forget the year ever happened, and fast-forward- " he checked his watch – "96 minutes to 2010, which will hopefully be less of a train wreck."

"Fast-forward by drinking?"

He clinked his glass against hers, "Cheers to that."

Bemused, she sipped her drink and let her inner responsible self be quenched by the alcohol. Jess had a point. Perhaps he could not give her sympathy, but he could give her whiskey. Maybe that was what she needed.

The band struck up their first song, and Rory found herself drawn into their eclectic beats, certain chords reminiscing of the eighties and nineties greats that she and her mother loved, mixed with an intangible futuristic sound made up of something electronic and deep. Jess stayed dark, still, and silent against the wall, his attention focused on the band, his hand gripping his glass. She closed her eyes and let herself feel it.

The night began to pass by in a whirlwind of music and crowds and raucous celebration that she ignored because it felt disruptive to the band. Before she knew it, Rory was having trouble standing upright, and took Jess' place leaning against the wall. She heard the countdown to New Years, and watched various couples kiss and celebrate 2010. She watched Jess down a shot of whiskey and nearly break it when he set it down, hard. She felt a detached sympathy for him, but she pushed it gently out of her mind.

"Ready to go?" he asked after the band finished their last song, leaning close to her ear. His voice was flat, controlled, as if he were suppressing the anger that she could see in the tension of his posture.

She nodded. He reached for her hand and began to pull her through the crowd of loud and inebriated people, keeping a firm grip on her even as she stumbled and tripped. She struggled to keep up, but he did not let her go.

The blast of icy winter wind was a rude awakening, and Rory blinked, bleary-eyed, at the sudden cold. Jess moved his arm to her waist, guiding her up the stairs, strong and steady. She leaned on him too much, but she couldn't help it. The city was spinning. The night was spinning.

"Taxi!" She heard him yell, gesturing at a car moving up the street.

"Jess," she mumbled. She held on to him. He smelled familiar, like pine trees and whiskey and libraries.

"Here's your ride," he tightened his grip on her waist as she slipped on a patch of ice, "what's your address? Brooklyn, right? Where's your phone?"

"In my bag," Rory said, yawning. She remembered most of her address. She told it to Jess.

"Rory, you're a mess," he sighed.

"How are you _not_ a mess?" she retorted. Her head was spinning.

He held her at arm's length, looking into her eyes. Rory stared back, swaying. He looked furious, but it was not directed at her. He was angry at the world, again. Angry at everything.

Unable to stop herself, she reached up to brush his cheekbone with her hand, feeling the hurt that emanated from him in dark, choking waves. Jess sighed. He pulled her close, wrapping his arms around her and resting his forehead against hers, his eyes closed. "Thanks for the whiskey and sympathy," he said, his voice low.

"You're welcome," she said, her voice cracking and barely audible, overwhelmed by his closeness. "You too."

Jess stayed there for a moment, his nose lightly brushing against hers, his arms strong around her frame. Then he pushed away, turned her around, and slid her into the cab, careful not to hurt her against the doorframe. He repeated the address to the cab driver. "Rory, you text me when you're back in your apartment," he said, like a warning.

"Will do," she said. She closed her eyes and leaned her head back.

"Can you make sure she gets in okay?" he asked the cab driver. Rory blinked and saw him hand the driver a wad of bills.

The next time she blinked, she was back in Brooklyn, outside her apartment. Jess, and his familiar scent of pine trees, was long gone. The cab driver waited while she struggled to unlock her door.

When she got into her room she collapsed on her bed, reaching with grasping fingers for her phone. With great effort, she texted him. _Made it_.

Jess' reply was immediate. _Good._

She reread it a few times, a smile tugging at the corners of her lips despite the misery she could feel aching in her stomach. Then she closed her eyes and wished the last year away.

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 **Back again after a long break, with some momentum and some inspiration. Thank you readers - the email notifications of reviews and favorites were what kept this alive even as winter and spring came and went. I hope you enjoy this!**


	5. Chapter 5: Father's Day 2010

Alright y'all. I know it's been a long minute. I won't list excuses - my last year has been a lot. But this has always been simmering on the back burner, and hopefully now I can make good on my promise to never leave a story unfinished. Better late than never?

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* * *

 **Chapter 5**

 **Father's Day Weekend, 2010**

Jess sat on a stool at the counter of the diner, nursing a coffee and watching Luke take measurements of every conceivable surface with a scuffed tape measurer. Luke was muttering under his breath, occasionally scribbling numbers on a pad of paper near the register. "Four by .. no, four and a quarter … no, four…"

"You could just estimate and see what happens," Jess suggested. He had a headache, and just barely managed to keep his sarcasm on the nice side of obnoxious.

Luke looked up at him, stern. "Are you completely crazy?"

"Why aren't you having a contractor do this?"

"Because then why wouldn't I just hire a chef to make the food? And a manager to run the place? And a barista to brew the coffee? And hell, a bouncer to keep out the Taylors of the world?"

Jess nodded, "Yeah, those are all great ideas. Do those too."

Luke scowled at him. "The _point_ is that I am more than capable of doing this renovation by myself. What kind of man would I be if I couldn't do a little bit of floor repair? And what kind of business owner would I be if I just hired a bunch of young idiots your age to run this place? Honestly, Jess."

"Hey, if I remember correctly, you called me - a young idiot - to come help you get this stupid project done."

Luke ignored him. He got on his hands and knees and began measuring the dimensions of the floor behind the counter. Jess groaned and put his head in his hands. His coffee was cold. He needed pain meds for his headache. Actually, if he really thought about it, he probably needed about twelve hours of sleep, a decent meal, and to lay off his excessive reliance on alcohol and cigarettes, but screw it, some ibuprofen could probably do the trick.

Jess knew he'd let himself go to hell the last few months, but habits were hard to change and he didn't really see the point in trying. He suspected that he had lost some weight, and he felt sick most of the time due to a likely combination of a hangover and nicotine poisoning. He drank too much coffee, stayed up half the night writing, and maintained a largely empty refrigerator and empty social life. In the late hours of the night he tortured his characters; he spun out plotlines that tangled into knots, pushed them to untimely ends and miserable conflicts, and took a kind of voyeuristic pleasure in shattering their love stories and ambitions. There was no great artistry in this heartache.

He was a mess, but he was a functional mess. His paid his bills. He showed up to work (sometimes late, usually hungover). He answered Luke's calls. He knew this was a phase – something that he would exist through, something that would gradually end.

It wasn't about Emma – Jess was clear about that. Sure, he was pissed off, and wished her nothing but ill will, but he would not give her full credit for the smog that had entered his life, choking his initiative, smothering that tiny, underused part of his brain that sought out happiness. It was more like, after years of steady progress, of upward movement, of growing and maturing, and being punched in the gut nonetheless, Jess was exhausted. He stalled. He gave himself months of regression. He sunk into the Hemingway-esque depression that always lingered on the edges of his subconscious, that he had repressed for years but that always called to him, whispered reminders of the hellhole that he grew up in, of the psychological damage that he knew he had probably incurred but chose to largely ignore.

Luke had put up with it with fairly impressive grace. After Jess didn't show up on Christmas, Luke clued into the situation pretty quickly. He called Jess every two weeks, asking how he was doing, what he was eating, if he needed anything. Jess gave him multiple-word answers because he didn't want the man to drive up to Philadelphia.

But now, in June, six months later, Jess was suspecting that Luke was fed up with it. He had called Jess the week before and asked that Jess take a long weekend to help him repair the diner floor. Jess had mulled it over for a few days, but eventually, begrudgingly, called Luke back and agreed to lend him a hand. Jess knew it was time for him to start to pull himself together. But it would take time to force the light through, to push the wisps of depression back to the sidelines, to regain and re-conquer the ground that he had lost.

"Alright," Luke stood, hands gripping the hem of his tattered flannel shirt, surveying the floor, "I think we're ready to hit the hardware store."

"Hooray," Jess said flatly. He chugged the rest of his coffee and stood to leave.

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The 'floor renovation' that Luke had bemoaned over the phone turned out to be only a few floorboards, rotted due to a twenty-year leak from a coffee maker that could have been called antique before Jess' birth. They weren't integral to the structure of the building. Luke could have replaced them by himself in a couple hours. But, nevertheless, Jess joined him at the hardware store, made sardonic and inappropriate comments about Luke's obsessive interest in wood, and obligingly carried the lumber out to the truck. He squinted in the sunlight and rubbed his eyes. He had done his best to avoid the sun for the last few months.

Luke climbed in the truck and rubbed his hands together. "Floor should be good as new by this afternoon. 'Bout time – Cesar has been threatening to quit over hostile work conditions."

"You are pretty hostile."

"No, the floor, _Jess_ ," Luke shifted the truck into gear and pulled out of the parking lot, shooting him a look, "hey while you're here let's get you a doctor's appointment, I think there's a disconnect happening somewhere between ear and brain."

Jess snorted. "I feel like this truck is a hostile work environment."

"Oh I can make it a hostile environment," Luke threatened. But his eyes were warm. He let the conversation drop, reaching to turn the music up. Jess leaned his head back and closed his eyes.

They fixed the floor quickly, with minimal hassle. Jess helped tear out the rotten boards, welcoming the strain in his muscles and the sweat that beaded on his forehead. He threw the old boards out on the sidewalk, almost hoping that Taylor Doose would come to confront them. But the streets stayed surprisingly quiet. Most people – to Jess' surprise – respected the 'closed for repairs' sign that Luke had taped to the front door. He almost wondered if Luke had paid them off.

They cut and fitted the new boards, installed them, and then stained them to match the rest of the floor. It looked mismatched anyways, but Luke shrugged. "It's behind the counter. Who cares."

Jess swept up the sawdust and debris, and helped toss Luke's tools in the back of the truck. Luke poured him another mug of coffee. "Free coffee for life, on me, for your labor."

"Thanks," Jess said. He leaned on the counter. He stared at the coffee, but he was craving a cigarette.

"Hey I had an idea, since this only took today," Luke began. His tone was conversational, but Jess narrowed his eyes at the subtle, planned tone in his uncle's voice.

"What if we took the evening and tomorrow and went up to the lake and went fishing? I know you don't have to be back until Monday – it's just starting to get nice up there. And Lorelai is at her parents' for Father's Day so I don't have anything happening here. What do you say? Could be a nice chance to, uh, unwind…" he trailed off, looking at Jess.

Jess thought about it quickly, but couldn't come up with a decent excuse since it was damn true that he had told Luke he could be here until Monday. He swore under his breath. "Alright, fine."

Luke beamed and clapped him on the shoulder, "That's great! Let me go grab a bag, and some gear, and the rods. Finish your coffee, we'll leave in an hour."

Jess tipped his mug to him, barely clinging to the strings of acceptable sarcasm. But Luke, clearly pleased that his plan had worked, didn't notice. Jess returned to staring into the black depths of the coffee. Probably, this trip would be good for him, in that whole heal-your-soul, get-into-nature, hippie bullshit kind of way. But Jess didn't have enough cigarettes to get through a couple days in nature with Luke, and he certainly didn't have the social capacity to sit by a campfire and _talk_.

He sighed. He drank the coffee. Too late now.

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Although Jess had never really been one for nature, the lake was beautiful in that quiet, East Coast, wooded sort of way. The water was a clear, tranquil blue, a pale, shimmering mirror of the June sky. Tall pine trees and long yellow grasses bordered the water, marching back into an indecipherable sea of forest. Luke's spot – a patch of grassy land near the north side of the shore – was hidden from plain view by a convenient clump of thick trees and brambles. Jess was sure that there were other people around, but he couldn't hear a sound other than the calls of the birds and the breeze that whispered through the branches, tugging at leaves and pine needles, sweeping ripples over the reflective surface of the water.

Luke set up a tent and a couple of beat up, old camp chairs. Jess threw some old, brittle sticks and larger branches into what was clearly an old fire pit in the center of the campsite, blackened with ash.

As evening fell the two men sat by the crackling fire, nursing beers and watching the last light of the day play out, both in the sky and on the shimmering lake. Jess gazed out, eyes unfocused, wrapped in his own thoughts.

"You know," Luke said, conversationally, "you should come out here more often, hit the lake, get out of the city. Lorelai absolutely refuses, and I like to avoid TJ as a rule. It's nice not being out here by myself."

Jess stretched his legs. "I like the city."

"Well sure, but don't you ever feel like you need to get out, to catch your breath?"

Jess remembered the ceiling of his room in his apartment. He had it just about memorized by now, every crack and paint chip, every change in coloration that reminisced of old water damage or faded paint. He had lain on his bed, staring up at the ceiling, hands behind his head, for hours every week over the last few months. He let his eyes roam the ceiling while his mind wandered, spinning, feverish. If he needed to, he could have drawn that ceiling down to the last, minute detail right there, in the dirt on the side of the lake.

Jess shrugged, shaking off the disturbing thought. "I guess. Sometimes."

"I'll start inviting you more often," Luke said. He stared back out over the lake, a hint of a smile just barely visible in the lines of his face.

Jess took a drink from his beer. He could feel the starting pains of a headache in his right temple, a dull, throbbing reminder. He ignored it.

Luke stayed silent for a long while, sipping his beer and watching the light gradually fade towards the western horizon. The sky became a deep, inky blue, stars beginning to twinkle as the last dregs of light clung to the surface of the lake, slowly dissolving into darkness. Jess tugged his jacket closer around him, burying his hands in his pockets and hunching his shoulders against the cold. Luke threw another log on the fire.

Luke handed Jess another beer, and cracked one open for himself. He cleared his throat. "I uh, I actually have been meaning to talk something over with you."

Jess glanced at him, raising one eyebrow.

Luke took off his baseball cap, twisting it in his hands. "Things are … things are going pretty good with Lorelai. Better than last time. And I know that the last engagement was, well, a disaster, but it's starting to feel like it's time that we tried it again. And maybe it's stupid to throw something like that in the mix when things have been going so well, but it just seems like the right thing. I don't know." Luke rested his elbows on his knees, gruff and a little self-conscious. "What do you think? You're good at telling me when I'm being a moron."

He could feel the tension in Luke's pause, waiting for affirmation. He rolled his eyes at his uncle. "Of course you should propose already."

Luke cracked a grin, relieved. "You think so?"

"She's an absolute nutcase," Jess warned. "But you seem to know that already. Neither of you are going anywhere, you might as well make it official."

Luke leaned back, smiling. "I just needed to hear it from somebody else, before I bungled this up again. I'm just ready, you know? I'm not getting any younger. Seems stupid that we haven't made this happen yet."

Jess nodded. "Definitely overdue."

"And she's dropped a hint or two," Luke added, building his case. "Of course she doesn't say anything serious ever, because why would that woman ever get to the point, so half the time I'm sure she's just giving me crap and talking out loud for her own entertainment, but I'm getting the sense that she's thought about it too. She keeps suggesting long term _vacation_ plans. Like either of us is capable of ever taking a vacation." He seemed scandalized by the very idea.

"Is she doing better?" Jess asked bluntly. He hadn't noticed much improvement with Lorelai since last summer, when Luke was recovering from his broken leg. Around the holidays she'd had that blow out with Rory, and when Jess had seen her in April she still had worry lines around her eyes and jabbered pop culture references a bit _too_ quickly and automatically.

Luke shrugged. "Yes, and no. She isn't talking to Rory much but at least her job has settled down. I think she's waiting it out, playing the long game. Rory will figure it out eventually. Everyone goes through that in their twenties."

Jess was suspicious that the last comment was vaguely directed at him, and his current pathetically unhealthy state, so he sidestepped his own line of conversation. "What's your timeline?"

"Soon," Luke took a swig of his beer. "I've got the proposal all planned out too – nothing too fancy or crazy, but it'll make her laugh. I think to make it work I'll need to get Kirk in on it ... which could be a terrible idea but I'm hoping this will be one of those rare times that he follows directions. We'll see if . . . "

Luke continued on, thinking out loud about his proposal plan and throwing occasional veiled shots at both Kirk and Taylor. Jess's eyes unfocused as he stared out at the darkening lake, occasionally nodding in agreement with whatever Luke was saying but mostly treading water deep in his own thoughts.

Luke was getting engaged again, this time undoubtedly for good. It wasn't surprising to Jess. But it made his inner ache - usually caused by the burn of whiskey, coffee, and cigarettes without a decent meal - twinge a little more harshly. Engagement was distasteful to him already, with all of the pomp and circumstance and the overproduced monotony of weddings, but he saw through all of that the real strings of emotion and companionship that wound tightly around Luke and Lorelai. The engagement was a fine next step, sure, but the real thing that made Jess grip his beer can more tightly was the fact that Luke was finally confident enough to live with a Lorelai, torn up over her daughter, and still maintain a relationship healthy enough to move forward. Something deeper seemed to bind them now, a quiet confidence in the happiness of finding a soul that matched your own and knowing it was meant to last. Jess could see quite clearly, through Luke's rambling, how deeply he cared for Lorelai and how much he longed to put her back to her usual bubbly, word-spewing, wisecracking self. And how even if Lorelai was only mostly there, her happiness temporarily strained, Luke still wanted every bit of her. And she would come back eventually. Luke would be sure of that.

Jess felt a little disgusted, as he turned over his uncle's relationship in his mind. But it was only because it reminded him of how dark and isolated his apartment was, how he had memorized the water damage in his bedroom ceiling from staring up at it, soaking in his own distaste for life. He was sick of himself.

He pulled himself back to reality, enough to hear Luke say, "I'm glad you think it's a good idea. I was worried this was bad timing, what with everything that has been going on."

"Everything can always be bad timing," Jess said. "But I don't think you can pick bad timing for this."

Luke half smiled. "I'll let you know how it goes."

"Can't wait," Jess said. His tone was mostly sarcastic, but he knew Luke would see through it.

Luke stood, tossing his beer can in the back of his truck. "I'm calling it."

"I'm going to stay here for a bit," Jess said. He felt his usual moodiness starting to increase, the dark of the night and his Uncle's news pressing down on him.

Luke evaluated him for a moment. "Alright. See you in the morning."

Jess tipped his beer can towards him. Luke disappeared into his tent, zipping it closed and fumbling with his sleeping bag. After a while it all fell quiet. Jess could hear the sounds of the night around him, the lake lapping quietly at the shore, the grass rustling. Insects chirped. It was very dark, and the fire began to smolder down to the coals. He thought about throwing another log on the fire but decided to wait, preferring the low, red smolder over the bright yellow crackle of a recently fed flame.

He felt his insides twist further, wringing out slowly, painfully. He sipped his beer and brooded.

Perhaps Luke's news had shaken him more than he wanted to admit, pulling him briefly from under the waters of self-destruction and showing him the way the world could look when it was bright and untainted by depressants and sleep deprivation and nihilistic authorship. His mind was fast, racing, as he stared out over the dark and silent lake. He could picture it, Luke living with a woman who had been a shell of her usual vibrancy for nearly a year now and still planning a life with her, supporting her, brightening her day both unintentionally and deliberately. Although Jess was internally quite sour, he was still unexpectedly touched by the simple beauty of Luke's desire to propose despite Lorelai's ongoing pain.

Jess had never had a partner who could grapple with his moodiness. All of his past relationships had been complex and satisfying and destructive and shattering, but in each of them he had felt the urge to shutter his darkness, to expunge it in prose in the early hours of the morning while whichever woman it was slept deeply and knew nothing of his emotive catastrophes. He tried, at least, not to share that inner part of him that was depressing at best and violently self-destructive at worst. He knew they suspected it. But he was also wary of sharing it, because he knew that his baggage came from a predictable montage of child abandonment, daddy issue clichés that hardened his heart to people but made him a damn good artist. All the best artists spent half the time choking on their own misery, after all.

Emma - _cheating asshole_ \- was his latest attempt at intimacy that unraveled into a heartbreak muse for literary purposes. And she was the main reason he was in this damn camping chair, freezing hands grasping a cheap domestic beer can, stuck in the woods so Luke could try to force him back to whatever reasonable form of adulthood he attained before his latest romance kicked him in the gut.

He drained his beer and chucked it in the back of Luke's truck. It tasted like shit, but it was there and available.

If he was honest with himself, his thing with Emma never had a chance of working out. And Luke's plans to propose to Lorelai made that very clear to him. Not only had he not wanted to share his internal brooding with Emma, but she didn't want a damn thing to do with it. She liked his seriousness, his unaffected charisma and his dark artistic tendencies, but she didn't like grappling with anything deeper than the surface level of his intricacy. She enjoyed the act of his writing but she didn't want to read it; she liked his body posture as he tortured himself over a manuscript but she didn't want to know the reasons for the knots in his shoulders and the terse tapping of his foot. She liked the background noise of his music but she never internalized the lyrics. And as time went on, and he lived an act of competent contentedness, she gradually became bored with the façade and the shit it hid. When he escaped to indulge himself in his writing for weeks in New York - to let his true inner sardonic shine - she tried her best to forget him and find joy and satisfaction in whatever other guy in dark skinny jeans made cute smiles at her in the break room. She wanted the _image_ of a guy like Jess - she didn't want Jess himself.

But, like the sucker for pain that he was, Jess had still grown attached to her. _Love_ might be too strong of a word, but he knew something deep had gutted him and put him in this state for the last months. He was tired of getting over it.

His other early relationships had been variations on the same theme. He played the other man once or twice, always disappointed in himself but enjoying the magnetic pull he could exude when things were complicated and wrong. But he always faced the same result. At his core he was an artist who needed to bleed to make a manuscript, and women never wanted to see the real gore behind literary fiction.

Rory . . . Rory was maybe the only exception. Jess stretched his legs out, unwilling to access the locked part of his teenaged heart that held _that_ breakup. But Rory, as a woman who loved great literature for what it inherently was, knew intimately the process that went into creating works that bled for decades to come. She lived for the hunger and the longing strung through the chords of great fiction.

They were too young when they dated for Jess to know how she would handle his usual state. For the most part he was a smooth talking, high functioning, nearly alcoholic entrepreneur and writer, but like any artist he had to break himself up to create. Emma and his other girlfriends couldn't handle that. But Rory, at least from what he remembered of her naïve, high school self, had analyzed his self destruction and told him to create something out of it. She acknowledged that he bled and challenged him to channel it into greatness. She expected more out of him. And when he saw her on New Years, she seemed perfectly fine to let him focus on the cyclone of anger that tore through his veins. He knew he hadn't been great company that night, but he appreciated her for draining the bar with him and letting him deconstruct. And - as was clear from her and Lorelai's ongoing issues - Rory was just as much of a fucking mess as he was right now, if not more so.

In the last months he had only barely maintained whatever semblance of a friendship he had with Rory. It wasn't her fault - she got the same treatment he had given everyone else. But he nevertheless knew that she probably noticed that he responded in one-word answers to her book recommendations and exclusively texted her quotes from literature's darkest alcoholic spirals. _So it goes_ , he typed, often, channeling Vonnegut's dead indifference. But she had observed his state on New Years, and she herself was wrapped in some kind of quarter life crisis, so he presumed she didn't care much about the lack of quality control in their conversations.

He could only guess if she would handle his adult self differently than his other girlfriends, now that he was generally put together but still prone to bouts of depressive artistry. Then again, she had read his manuscript with the empathy and expertise of a Jess-fluent, experienced editor. And he had thanked her for making him bleed.

He shook his head, heavy and tired. Luke was right to bring him out to this godforsaken lake, as much as Jess may have resented being caught in his uncle's plan. It was high time for him to pull himself out of his slump. The upward track loomed long and challenging ahead of him, but he knew it was the only choice.

Jess stayed in the chair for a few more hours, hands itching for a pad of paper or his laptop to torment his characters, but as he had neither he let the prose write and rewrite itself on the surface of the lake.

.

.

When they returned from camping Jess helped Luke unload the gear and pack it away. He also let Luke make him a full meal for lunch, and resisted the urge to follow it with a cigarette. Instead he drank a glass of water and poured himself a cup of coffee, feeling overly wholesome and also just weary enough of feeling like shit all of the time not to care.

He hugged his uncle goodbye - a tight, one-armed squeeze and a strong clap on the back - and wished him luck. He told Luke to call him when it happened, or better yet have Lorelai call because Jess knew who the true storyteller was in that relationship. Luke agreed, his eyes warm despite the usual gruff expression on his face.

Jess walked out, swinging the his car keys around his finger, squinting less-resentfully in the bright sunlight. When his eyes adjusted, he saw a familiar head of dark hair across the street.

He hesitated, and tilted his head. When she paused to read a sign on a post, her profile visible, he confirmed that it was Rory and walked across the street without checking for cars.

"Hey." He caught her attention, standing a few feet behind her.

She turned and raised her eyebrows, surprised to see him. "Oh - hi. What are you doing here?"

She looked uncomfortable at being caught and a little worse for wear. Her hair was messy and she was wearing one of Lane's band t-shirts. But her posture was defiant and the lack of bags under her eyes made it clear that she was abusing herself less than Jess was. _She_ probably still did responsible things like eat breakfast and sleep properly and not pick up a cigarette habit.

"Luke," Jess thumbed towards the diner, "used a weekend floor renovation as a ruse to make me go camping with him and 'experience nature.' Why are you here?"

"Oh," she looked down at her feet, "uh, living with Lane for a minute, actually. I sublet my apartment in New York to try to pay back my grandparents some rent."

Jess appraised her, not very surprised. It made sense that she would escape to Stars Hollow after being chewed up and spit out by New York City unemployment and the consequential family fallout. But he was also a bit disappointed. He'd told her, not subtly, to get a job and start paying rent. Her current plan seemed like another step in parachuting her way through the realities of life and jobs and adulthood.

"I'm paying Lane too," she clarified, as though she could read his mind. It didn't help much.

Her comment made him think that maybe she was offended at the tough love he had given her on New Years. But then again, _she_ had texted _him_ , and Jess had never been one to sugarcoat anything. He laid it all out for her, usually uncensored and unfiltered, because he knew she could handle it and because she definitely needed to hear it. The sheltered Rory of his high school days had needed it, and the grown up Rory floundering now needed it.

Still, Jess was tactful. There was a time and a place for brutal honesty, and Rory on the sidewalk right now, caught living on her best friend's couch, seemed to already know the truths he could lay on her. Her eyes were defensive.

"Listen," he said, knowing he needed to get on the road and get back to work, "if you ever need a break from this place and want to visit Philly, I know a bar good for reading and commiserating."

She gave him a wry smile. "Whiskey and sympathy?"

"Whiskey always," he shrugged. "I can say sympathy but we both know it's not my strong suit."

"Whiskey and commiserating then," Rory agreed. "I'll let you know if and when I finally crack here."

He nodded, looked at her one more time, and then turned and headed back to his car. He could feel her eyes on him as he started the ignition and pulled away from the diner, fingers drumming the wheel.

Jess felt his gears begin to turn, thoughtfully, delicately. The inner artist in him quit throwing matches on his manuscripts. Rory's lone figure, arms tightly crossed, standing on a street in Stars Hollow with no particular direction to go, stayed locked in his mind.

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	6. Chapter 6: Halloween 2010

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 **Chapter 6**

 **Halloween, 2010**

By October, Rory knew she had overstayed her welcome at Lane's. The twins called her "Auntie" but Lane and Zack both joked that she was their third kid. She tried to be helpful - she paid Lane and Zack rent every month, cleaned often, ordered take out (not wanting to subject them to Gilmore cooking), and frequently babysat Steve and Kwan. But the fact of the matter was that she was on the downward slide of her mid-twenties and she shouldn't be sleeping on a couch covered in legos and crayons.

Her last few months had constituted an impressive show of paralyzing inaction. Rory made enough money from subletting her New York apartment that she could afford to pay Lane and not run out of health insurance or food, but it wasn't a comfortable existence. Worse were the calls she would get from her mother all the time. Lorelai alternated between wheedling her to come home - "Rory, come on, we can order pizza and go through and the classifieds - I saw some great positions the other day, including a Veterinary Acupuncturist _and_ , get this, some charming little family-run place called 'Big Daddy's' has a dancer position open and we both know how much you _loved_ to tap as a kid" - to using her most serious, disappointed mother approach: "Rory, living off of your friend who has two young kids to deal with is almost worse than taking your grandparents' money! Come home, it's free, we can figure this out. But you can't do this to Lane. I'm really worried about you, I wish you'd come home so we could work on this together…"

Rory didn't fall for either tactic. She tried to be patient, to assure her mom that she was being inordinately helpful at Lane's and that she had a plan and all of this was just temporary, but she could tell Lorelai was devastated at her distance. If there was one thing Rory was not good at, it was handling failure. And she didn't want her mom to witness that.

As the late summer transitioned into fall, and the beautiful Connecticut foliage grew into vivid shades of orange and yellow in the crisp fall air, Rory began making moves, compromising her vision for her reality. She applied to other jobs in New York, and managed to get hired by a tutoring company for private school kids. She told her subletter that she'd be taking her apartment back at the end of October. And she resisted seeing her mother until she had good news, or as Emily liked to say pointedly whenever Rory drove to Hartford to quietly suffer through dinner, " _a career_."

On Halloween, Rory packed up Zack's car with all of her stuff and promised to be back in a couple days to return it. She felt a bit like Kerouac: _Our battered suitcases were piled on the sidewalk again; we had longer ways to go. But no matter, the road is life_.

Lane gave her a tight hug, "Please don't get scammed by the New York parking lots. Come back anytime. Steve and Kwan are going to miss you."

Steve and Kwan were currently running around the yard. Upon hearing his name Steve stopped suddenly and stared at Rory and Lane, causing Kwan to run into him. Both boys tumbled to the ground, looked at each other, and burst into giggles.

"Seems like they'll be just fine without me," Rory smiled, "although hey, I think I really figured out that Steve is going to be your heavy rock guy and Kwan is going to be more of your alternative, indie boy."

Lane appraised her sons. "I could see that. Steve started head banging at two."

"A true metal head," Rory nodded.

"And Zack taught him how to do devil's horns with his hand. He flashed that one for his preschool photo."

Rory snorted. "Course he did. Thumbs-up is so overrated at this point."

Lane sighed, glancing at her other son. "But, Kwan is the drummer, and we both know how drummers are."

"Straight up trouble," Zack interrupted their conversation, grinning and throwing an arm around Lane's soldiers. "If Kwan's the drummer, he's also the front man. Boy's got some pipes."

As if to emphasize this, Kwan tripped again, fell to the ground, and, upon observing adults watching him, immediately burst into tears. Rory tilted her head. The kid's wails were surprisingly on pitch.

Zack hurried to scoop up his kid, and Rory gave Lane one more hug. "Thanks again, for everything. I really mean it. I know I've been a mess lately but you guys have really saved me the last few months. Forever in your debt."

Lane waved her off, "You can stay anytime. Text me when you get there."

Rory waved at the twins, "Bye boys. Rock on, little angels."

Steve gave her a solemn, one-handed rocker devil's horns, and Kwan waved cheerfully.

She climbed in the car and put the key in the ignition, hearing the old engine rattle and bang to life. The car shuddered violently, as if shaking itself from sleep, before mellowing into a quiet roar with infrequent hiccups and crashing noises. Zack grimaced and shouted, "If she breaks down, just give me a call!"

Rory gestured in agreement and then pulled the car away from the curb. She rounded the little town square, which was crammed with hay bales and pumpkins and scare crows and other Halloween décor. She could see Taylor Doose standing on the gazebo steps, shouting instructions down to a crowd of lackeys, Kirk foremost among them with a clipboard and a quizzical expression on his face. She knew that tonight would be trick-or-treating and apple cider and town ghost stories and all of the quirky bits and pieces that she loved most about her little hometown, but she couldn't bear to stay for it. Lane had offered to let her take the boys trick-or-treating (Steve was going as Gene Simmons and Kwan was going as Freddie Mercury), but Rory had declined, feeling undeserving to join in on lighthearted, weird, small town fun when she lived as a sort of tribal nomad on Lane's couch.

She exhaled heavily, surprised at the tension that released from her shoulders, as soon as she turned out of Stars Hollow and onto the Connecticut road that gradually joined up with the interstates that all funneled naturally to New York City, like streams chattering towards the ocean.

The trip was slow - it seemed like traffic into the city started halfway through Connecticut - but she didn't mind. She stared ahead at the road, her mind full, chewing on her bottom lip. She wasn't sure how she felt about getting back to her Brooklyn apartment, but she knew it was the right thing to do. Maybe this time her knick-knacky furniture and string lights would be exactly what she needed. Maybe she would enjoy tutoring Upper East Side private school kids, destined for Harvard and Yale and Princeton in all of their Ivy League, privileged, school-uniformed glory. Maybe she'd get a phone call tomorrow from a publishing company seeking her help. Or maybe in three months, when she inevitably ran out of money, she'd be back driving Zack's car to Lane's couch.

She shook her head, trying not to let mental images of her destitute future self mess up her return to Manhattan. But it gnawed at her.

Soon enough she was driving through New Rochelle, then the Bronx, and finally the skyline of the city rose in front of her. The sun was golden in the mid-afternoon, illuminating the fall foliage that peeked through the heavy urban sprawl. Rory's stomach clenched. She gripped the steering wheel, careful as she maneuvered through the thick traffic, feeling her heartbeat quicken to match the pace of the city, her slow Stars Hollow pulse long gone.

Rory stared at the city ahead of her, glimmering in that golden hour, indifferent to whether she stayed or left. Cars honked. And something deep inside of her recoiled - her confidence was shaky, not certain. She felt her body get more and more queasy as the car inched towards the skyscrapers, descending into the metropolitan madness.

Abruptly, as if realizing she'd forgot something, she switched two lanes, exited towards Washington Heights, and took the George Washington bridge across to New Jersey, the opposite direction of her Brooklyn apartment. The water of the Hudson glimmered beneath her.

She let out a nervous laugh. She had no idea what she was doing. If she stayed on the I-95 south it would eventually take her to Philadelphia.

Rory glanced at the city in her rearview mirror. She let the interstate carry her on.

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By the time Rory reached Philly it was around six o'clock, the sky darkening, and she was thoroughly doubting her impulsivity. Jess could be out of town, or busy. But, more likely than not, he was holed up at his apartment or the publishing house or some bar somewhere, pen to paper, hair messy from running his hands through it too much, focused single-mindedly on his work. And he had told her to stop by Philadelphia whenever she snapped at Stars Hollow.

The last two times she had seen Jess he had seemed worse for the wear. When he caught up with her on the street in Stars Hollow in June he had looked exhausted, with dark bags under his eyes and the unhealthy, pale, drawn look of a man who stopped taking care of himself. But as always, he had looked at her as though he could see straight through her, dark eyes inscrutable, evaluative. And she knew he could have ripped her to pieces for living on Lane's couch - " _Really? Grandparents to Lane's?_ " - but he refrained. Instead, he had offered Philly as a refuge. And months later, after quite literally getting up off the couch, Rory was ready to take him up on it.

She took a few wrong turns on the way to Truncheon Books, but managed to find it as the sky turned an inky blue. Little trick-or-treaters wandered up the street, hand-in-hand with their parents, dressed as superheroes and monsters and animated movie characters. Rory smiled despite herself as she parked Zack's car. The early hours of Halloween, when the tiny kids that were Steve and Kwan's age got their candy before the older kids took to the streets, had always been her favorite.

Before she got out of the car she glanced at her reflection in her rearview mirror. Her hair was a damn mess from driving with her windows open, so she pulled it up into a haphazard knot. But her eyes were clear and she had a pink glow to her cheeks that she attributed to the nerves of driving two hours out of her way without even confirming that Jess was available.

Screw it, she decided. Worst case scenario, she drove back to Brooklyn.

Rory locked the car and hurried up the steps. The sign said _closed_ , so she rang the bell that she assumed was meant for the apartment upstairs. She knew Jess had moved back in above the publishing house in the last few months because Luke had closed his diner for a day in August to help him move, which meant Rory had stood on the step of Luke's, confronted with a closed sign, befuddled and not caffeinated and forced to berate Luke the next day about advanced notice for café closures.

She bit her lip again. Eventually, she heard footsteps and the door swung open.

Jess stood there. If he was surprised, he hid it masterfully. He leaned sideways against the doorframe, one hand drumming the door.

"Er, hi," she said, awkward.

"Hi." He assessed her. "You hungry?"

"Starved," she said gratefully. She meant it.

"I know a place," he opened the door wider. "Let me just grab my jacket."

She stepped into the entry of the publishing house, enjoying the smell of old books and something like a hint of whiskey. The main floor was mostly dark, closed for the day, but she could still see that the place was much busier than the last time she'd been there. They had more bookshelves now, stacked with materials, and the workspace in the back corner was overflowing with papers. If she squinted through the darkness she thought she could see Jess' books on one of the shelves.

He hurried back down the stairs, one hand holding a dark grey blazer and the other jangling keys. "Alright Gilmore, let's go."

They returned to the street. Rory motioned to her car, "Need me to drive?"

"Nah, we can walk," he gestured up the street, "after you."

Rory fell into step beside him. They maneuvered around the miniature trick-or-treaters. The area was mostly residential, but she could hear the sounds of revelry not too far off. "Where are we going?" she asked, curious and hungry.

"There's this one bar a few streets over that has decent food and good window seats," Jess replied. "It's a good night to people watch."

They passed a college-aged boy wearing a full Henry VIII costume, tights, turkey leg and all. "That it is," Rory agreed, nodding in approval.

He didn't seem to care too much why she was in Philadelphia, so Rory let the easy silence continue as they walked. She felt warm, happy. It seemed very natural to her to be strolling next to Jess, the chill of the night beginning to set in, leaves crunching under their feet.

After ten minutes they reached a busier area, a historical looking street lined with little red-brick restaurants and cafés and shops. String-lit patios, nearly closed for the winter, were full of adults in costumes pre-gaming their own Halloween festivities. Jess led her to a place on the corner with big floor-to-ceiling windows. It was dark inside, all exposed brick and mismatched tables and candlelight. Jess led her to two empty seats at a window-front counter.

"You always 'know a place,'" Rory said, impressed despite herself.

Jess shrugged. "Writing at home gets boring. And I'm not a fan of that where-should-we-go game where no one wants to make a decision and half an hour gets wasted and everyone feels like they're disappointing each other."

Rory also disliked that game. She smiled and accepted the menu that a waitress walked over and handed her.

"This looks great," she said honestly. She saw a cheeseburger on the menu and felt at home.

The waitress came back quickly and took their drink orders. Jess ordered something dark and whiskey-like, and Rory asked for a glass of red wine. Her last time drinking whiskey with Jess on New Years had ended with her nearly blacked-out and incapacitated by an excruciating hangover for two miserable days. She lived sprawled on her bathroom floor and drank water and gingerly ate saltines, watching the pattern of her shower curtain swim side to side. Thirty-six hours later, when she was properly detoxed, she had ordered about six grilled cheeses from the deli next door and watched reality TV and nearly cried she was so grateful to feel human again.

But, despite the overall unpleasantness of the whole experience, it had been the night and the fallout that she needed. Drinking with Jess had felt like a compounded assault of muted anger and unhappiness, each of them descending into their own self-disgusted spirals, wrapped up in short glasses of dark liquor and the grungy, loud beat of a tiny East Village venue where everyone was drinking to forget the last year. She had _needed_ to feel as crappy as she could, to hit the bottom of the barrel so to speak, and dear god had she found it, curled up on the cold tile of her bathroom floor, her body so miserable that she nearly considered taking herself to the hospital for an IV or a medically induced coma. It may have been just another heavy drinking night for Jess - he had outpaced her by a mile but somehow didn't need a cab driver to coddle him home - but for her it had been a proper, necessary cataclysm. She called her grandparents and asked them to stop sending her money the next day.

She sipped her wine. Thank god all that was over.

Jess put his elbow on the counter, resting his chin in his hand, eyeing her. "So you just in town, or what?"

" _There was nowhere to go but everywhere, keep rolling under the stars_ ," Rory quoted Kerouac. She shrugged. "I missed my exit for New York."

His half smile grew. "You missed your exit about two hours ago."

"Funny how that happens, huh." Rory kept her tone light, enjoying the banter. "Did I keep you from any big Halloween plans tonight?"

"Oh you know, the usual," Jess leaned back in his chair. "Witch burnings, wiccan poetry readings. I heard one of my favorite coffee shops was going to have a monster mash, but to be honest I'm more of a séance kind of guy."

Rory snorted. "I'm clearly interrupting you from some very important activities."

Jess shook his head. "No. Honestly, you're just interrupting me from a night of writing and whiskey, with the potential for an Edgar Allen Poe reading or two."

"Oh, good choice," she approved.

" _Once upon a midnight dreary, while I pondered weak and weary_ ," he recited "The Raven," slowly revolving his glass of whiskey. He glanced outside at the revelry, the warmth in his eyes belying the melancholy of his words.

Jess didn't look weak or weary anymore. Rory eyed him briefly, as his attention was focused outside, and was surprised at the change in him. He'd clearly gotten a hair cut; his dark hair was still a side-swept mess but in that easy, natural way that looked good on him rather than unkempt. He was no longer thin and pale. Rather, he seemed as though he was sleeping regularly, spending time in the sun, possibly eating meals. His skin had some color to it and his five o'clock shadow - no longer a five-day shadow - highlighted the sharp of his jaw line. His sleeves were rolled up in a casual sort of way and he seemed perfectly relaxed, sitting with her at the counter.

"Anything to eat?" The waitress returned, interrupting Rory's scattered thoughts.

Rory ordered a double-decker cheeseburger and extra fries. Jess, amused, told the waitress he'd have the same.

"So is your metabolism ever going to kick in, or do you have a lifetime ahead of you of eating enough food for multiple humans?"

"I've been driving _all day_ ," she protested. "And you've met my mother, what do you expect."

Jess took that as an acceptable answer, but his smile stayed, even as he drank his whiskey. "Alright, I have a game for us."

"A game?"

"Yeah," he gestured outside with his whiskey glass at the costumed passerby, "A point system of sorts. Five points for literary figures, obviously. Three for _actually decent_ artists or actors or musicians. Two for joke costumes that don't make you cringe too much."

"Four for miscellaneous greatness," Rory contributed.

Jess shot her a skeptical look, so she defended her position. "Henry VIII wouldn't have fit into any of your categories, and you know in your heart that he deserved four points."

"Fine," Jess agreed. "And one point for unbearable clichés."

She nodded in agreement but glanced again at him out of the corner of her eye. He was barely halfway through his glass, no longer drinking like he was trying to injure himself in a dark East Village bar on an icy night. Instead, he seemed to be enjoying himself, unbothered.

"Five for me," Jess pointed to a group on the street corner. "Alice."

A little girl, who looked about six or so, was indeed dressed like Alice in Wonderland, clutching a pillowcase of candy. Rory immediately rolled her eyes. "No way, come on, 'literary reference' doesn't count for an actual Disney princess."

"The Brothers Grimm would disagree," Jess countered. "Not to mention the right honorable Lewis Carroll."

"Completely unfair."

" _And hast thou slain the Jabberwock_?" Jess quoted, teasing. "Up your game, Gilmore."

Rory pretended to glower, but inside she felt buoyant. She sipped her wine and scanned the street. "There," she pointed across the street. "Harley Quinn. Five points."

"One point. Unbearable cliché." Jess dismissed her.

"Oh, so the pretentious bibliophile is opposed to graphic novels?"

"Not at all," he seemed insulted, "but come _on_."

She raised her eyebrows at him over her wine glass. "Five points."

Jess let her have it. The waitress delivered their food, and Rory was too interested in her cheeseburger to participate proficiently in the game. She let Jess rack up the points as she devoured her food.

"Honestly," he shook his head at her. He seemed vaguely impressed.

Rory didn't care. She pointed her elbow at the street in front of them. "One point for that egregious political statement."

Jess rolled his eyes at the idiot in the suit and the politician's mask that stood in front of them. Then he nodded across the street. "Three points for Stevie Nicks."

" _Nice_ ," Rory said, appreciatively.

Before long the waitress came to collect their plates, Rory's scraped clean and Jess' more or less taken care of. Rory sighed and leaned back, holding her wine glass. She felt full but wide awake, buoyant.

"So you were driving to New York, huh?" Jess said casually, as if continuing an ongoing conversation.

She nodded. "Yeah. Borrowed Zack's car to move back to Brooklyn."

"So you were _moving_ back to New York," he clarified.

"Yes," she said. She could tell her voice was a little high, but she pretended to be confident. "Felt like the right time."

"What are you going to be doing there?" he asked. "Oh, five points, Gandalf."

Rory snorted at the Gandalf, who was clearly inebriated and had just dropped his staff while trying to cross the street. They were getting to that slightly later time of night when middle school kids ran the candy circuit and adults who had started drinking in the middle of the day were beginning to make idiots of themselves. She saw more than a few groups of sorority girls begin to pass by, giggling and self-conscious, wearing various forms of leotards and animal ears.

She answered his question slowly. "Uh, working. I got a job as a tutor. And continuing to try to find an editing job. It was just time to try again."

Jess' slight smile grew. He signaled to the waitress to refill their glasses. "From what I remember, you're a terrible tutor."

"From what I remember, you're a terrible student," she retorted. "Five points. Beowulf."

Jess squinted into the night. "No way. That's Thor."

"No," Rory held firm, "Look, he's holding Grendel's arm. Come on, Jess, don't stereotype Scandinavian heroes, it's so offensive."

Jess saw the arm and chuckled. "Fine, five points to you. And fifteen points to that guy for originality. Also I fully disagree - I was a model student. From what I remember, _my tutor_ told me to keep driving around in circles instead of going back to study. And I do nothing if not obediently follow directions."

Rory laughed. "Well you're the one who coerced me into driving around in the first place. Besides, I'll be in Manhattan, none of my students will know how to drive."

"Alright, then you'll probably be a fine tutor," he amended. "Just don't tutor and drive."

She shook her head, highly amused. The wine was starting to get to her. "Two points. Couch potato. A for effort."

Jess ducked his head, nearly choking on his whiskey. The guy was wearing a horizontal refrigerator box with cushions stapled to it, and his face was painted brown like a potato.

"Or," Rory raised her eyebrow, self-deprecating but also in a wicked funny mood, "alternatively titled _Rory: A self portrait at 26_."

Jess appreciated her humor. He clinked his glass with hers. "Thank god that's over."

"What, being a couch potato?"

"No, 26." He glanced at her. "Right, your birthday was a few weeks ago?"

"Oh, right," she nodded. Her birthday had been extraordinarily uneventful. Lane had made her mac and cheese and she and Rory had indulged in a full bottle of wine and a showing of _Clueless_. "Being done with sleeping on a friend's couch is also nice."

He absorbed her words and sipped his whiskey. She turned slightly towards him, one knee brushing his unintentionally. "What about you? You seem better than when I saw you last."

Jess, she was sure, recognized and ignored her implication. "You caught me at a good time. Annual Poe appreciation day is always worth waking up for."

"No," Rory smiled, but stayed steadfastly on topic. "I mean it, you seem great. And last I saw you, you looked a bit like Luke had kept you in his car trunk for the weekend."

He acknowledged her with a tip of his shoulders, but he didn't look at her, his eyes fixed outside. " _I became insane, with long intervals of horrible sanity_."

"You _have_ been reading Poe," Rory rested her head in her hand, looking at him. She was curious. "No really, you seem better."

"I got a new idea for a book," he said indifferently. Then he quoted Poe again. " _Words have no power to impress the mind without the exquisite horror of their reality_."

Rory was fluent in both Jess's evasiveness and Edgar Allen Poe, so beneath the haunting quotations that he spun out over his whiskey, she recognized the undercurrent of an acknowledged prior depression. "How bad did it get?"

"Not bad, comparatively," he glanced at her, noticing her concern. "You know, a few months of alcoholism and insomnia. Damaged a few relationships - sorry for being a non-communicative asshole over text, by the way. But eventually it came time to pull it back together."

She hesitated, not sure how much she wanted to press him. Jess was notoriously difficult to pin down, and although he was good at brutal honesty, he was less capable of revealing his inner self in any sort of candid, non-sarcastic, straightforward way. But Rory could try. "And this all came about because of the cheating girlfriend?"

He took a swig of whiskey. "She helped."

Rory understood 'helped' to mean the opposite of its dictionary definition. "But there was more to it than that? Is your family okay?"

"Three points, Kurt Cobain," Jess craned his neck, trying to see across the dark street, "that might be Courtney with him, in which case six points."

She just sipped her wine, waiting.

" _And so being young and dipped in folly I fell in love with melancholy_ ," he quoted Poe again. Jess was in prime ambiguous form tonight. But then he swiveled towards her, resigned. "No, family is fine. I think I was just tired. It's been a lot of years of being on top of my game. Regression was inevitable."

Rory contemplated his words. "Regression was inevitable?"

"You never feel like that?" he raised an eyebrow.

"I think we grew up with different views," she said.

"Ah," he nodded, "right, golden child, rose petals lining your shining, pre-destined path to Yale, no room for failure."

Rory shot him an annoyed look. "Not that bad. But sure, sort of . . . failure's not really in the Rory Gilmore playbook. The family never seems to like it much. Three points, Donnie Darko."

Jess evaluated her. "But you're good now?"

" _I remained too much inside my head and ended up losing my mind_ ," she replied. He wasn't the only one who could quote Poe.

Jess appreciated this. And like her, he waited for her to answer the actual question.

"I'm getting there," she said, honestly, "I'm doing the steps. Getting the job, paying the bills. Maybe one day I'll get to do what I want, but I just don't know how."

Something struck her, and she drained her wine glass. "Jess, I'm so envious of you. How did you manage to make this happen? How do you get to spend your days writing and creating, doing what you love to do?"

He gave her a funny look. Rory knew she was taking this conversation down a slightly deeper path than Halloween games and careful, elusive banter, but she didn't care too much. She was only slightly dizzy from the wine, in that comfortable place where she became ignorant of everything around her, where she felt nearly sober but for her tunnel vision on the man in front of her. Her peripheral vision and ability to hear background noise were nearly gone.

"Writing isn't an option for me," he said, carefully, as if he were trying to come up with the right response to her question. "It's like - I could try not to. But even if I were at a desk job right now, I'd spend half the time working on my own stuff instead of my job. Or, if I couldn't do that, I'd sacrifice sleeping for writing. It's like a catharsis. You get it - it's like reading for us."

She heard the _us_ in his sentence and felt it deep, warming her. "So I feel like that with editing. But the problem is, I need things to edit. And I have no idea _how_ to make that happen without a single publisher even giving me an interview, or how to . . ."

Jess turned to look directly at her, and she swallowed her words. His eyebrows were furrowed, his dark eyes searching. She became uncomfortably aware of just how long his eyelashes were.

"Do you want to do me a favor?" He asked, abruptly.

"Sure," she said, not even thinking about it before she agreed, caught in the intensity of his gaze.

"Want to edit my current project?"

This time she heard him, internalized it, and barely let him finish speaking before saying an emphatic " _Yes_."

Jess's eyes twinkled. "I can't promise it's any good. You read my last trash manuscript, and somehow got it back on track. It would save me a lot of time and misery if you just did that chapter by chapter instead of me having to grapple with an entire novel constructed of crap and then send it to you for last-minute saving."

Rory nodded and felt her heart beat a little quicker, her mind already racing, imagining another opportunity to edit Jess' work. Her last experience with one of his manuscripts was undoubtedly the reason for her current unemployment and general life dissatisfaction, but she did not regret it in the slightest. Reading Jess' searing prose, digging through the layers of his haunted characters and connecting the lines of his intricate plots, had lit a spark deep in her soul and her intellect that she knew tutoring or article editing would never quite quench. She found herself missing the feeling of having a pen in hand and a great work before her, raw, newly developed by a talented artist. Above all else, she yearned to be _connected_ to that artistry, to be swept in the tide of modern literature and to help shape it, to work with writers like Jess who saw the world as an immense opportunity for poetry and pain and profound emotion and were able to translate those visions into literary monuments.

Jess tapped the counter. "I'll be right back."

He rose and disappeared, and Rory stared after him. She had an aching feeling in her chest. She couldn't tell if it was because of the opportunity he had just handed her, as nonchalantly as if he had asked her to run to the grocery store for him, or if it was something else.

She swallowed at _that_ thought and turned back towards the window. The night was getting truly sloppy now. A drunken clown was hunched over a trash can on the corner as his friends, who all appeared to have lost key aspects of their costumes, harassed him to keep walking.

But Rory couldn't shake her mind clear. She felt something different, something pulling at her. Jess was always a dark enigma: an artist that spoke to her nearly exclusively in literature and sarcasm; an old friend that made her feel like she was returning to a well-loved book; and, for years now, a more confident, slightly less reckless, smoother version of his younger, angrier self. He held a glass of whiskey like an indifferent habit and watched the world outside with dispassionate intensity, lacing lines of literature in his mind that she caught glimpses of in the tilts of his head and the way his eyes hungered at the world outside. If she asked, she was sure he would admit to identifying characters in passerby, analyzing drama in observed conversations, filing away the complexities and quirks of the human experience for future literary purposes.

Then again, for Jess, everything was for future literary purposes. He drank like Hemingway, demanded like Kerouac, and philosophized like Vonnegut. Although he claimed today was Poe appreciation day, she had seen Poe's melancholia wrapped up in his Spring depression. And, to her vague surprise, she felt fascinated by him, by his free artistry and the life of passion that he lived. He had what she wanted, even if he didn't appreciate it as deeply as she did, sitting at this bar next to a writer that lived and breathed his artistry.

Perhaps she was just in a cloud of nostalgia. It was a time of transition for her, a time of moving and life reconfiguring and recalibrating. And Jess was always Jess. Mary Shelley knew it best - _The companions of our childhood possess a certain power over our minds which hardly any later friend can obtain_.

He returned to his seat. Rory immediately and purposefully dropped her train of thought.

He pointed out the window. "Five points. Cat in the hat."

Rory grinned and leaned forward, arms on the counter, returning to the game.

They stayed for a while longer, mostly bantering and occasionally collecting points on the diversity of costumes that paraded before them. Rory felt cheerful, deeply grateful that she had missed her exit to Brooklyn and taken a chance on Philadelphia. She laughed more than she had in months, enjoying Jess' sardonic quips and quick wit. Eventually they paid and walked back to Truncheon books, the chill of the witching hour settling upon the streets of Philadelphia.

"You can stay here," Jess offered, concerned when she pulled her car keys out of her purse.

"No, it's okay," she said. She meant it. The wine had long worn off and she felt wide awake, energized by the night and the conversation. "There will be less traffic now anyways."

"Are you sure you're okay to drive?" He wasn't convinced.

"I'm fine," she promised.

He didn't seem too pleased about the prospect of her driving to New York at midnight, but he had never been one to tell her what to do. So, instead, he brought her into the publishing house for a minute, printed the first chapter of his current project, slid it into a manila envelope, and handed it to her. "Rip it to shreds."

"I do nothing if not obediently follow directions," she said, teasing, stealing his words from earlier.

Jess rolled his eyes. " _Quoth the Raven, 'Nevermore_.'"

She fought the urge to give him a brief hug, and instead waved, held the envelope tightly, and returned to Zack's car. When she started up the engine and flicked on her headlights she could see Jess, standing in the door of Truncheon books, arms folded, watching her.

She left his dark figure in the doorway and drove up the street, glancing one last time at him through the rearview mirror. Then she set her direction to the highway. She drove quickly through the night, occasionally glancing at the manila envelope on the seat beside her, fighting waves of excitement and nostalgia as the eastern seaboard flew by.

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Late the next morning, after Rory woke thoroughly dazed and confused in her Brooklyn apartment, she hurried to put on yoga pants and a sweatshirt and brush her teeth. Her hair was still in a knot and she hadn't worn mascara in months, but she didn't care much. She walked to her favorite coffee shop a few blocks away, took a seat by the window, and ordered a giant mug of steaming black coffee and a sesame bagel with veggie cream cheese. She pulled her favorite pens out of her purse, the fancy ones that scrawled dark ink seamlessly across the page that dried quick enough to prevent her from smearing everything in her excitement. Before she opened the envelope she took a deep breath and looked out the window. The sky was bright and blue in the November morning, hinting at the frosty winter to come, and the remaining leaves clung to the trees, fighting the breeze that threatened to tug them away.

She smiled despite herself. The coffee was strong, and she had a new chapter in front of her. Carefully, she pulled the sheaf of paper out of the envelope, uncapped her pen, and began reading, losing herself in Jess' fiction.

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* * *

Thank you all for your lovely feedback! I so appreciate your reviews :)


	7. Chapter 7: Christmas 2010

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 **Chapter 7**

 **Christmas 2010**

Jess felt oddly as though his life was picking up steam. Time seemed to flow rapidly, ravenously, surprising him when he would notice the date and realize it was already November, and then December. The publishing house was busy of course - Matthew and Chris complained endlessly but refused to hire extra help - but Jess knew that most of his hours were disappearing into his latest novel. Sometimes he felt dazed when he stood to stretch after hours of typing, his eyes strained by the light of his computer, unable to determine how long he had been working. It felt like coming up for air after being underwater, but Jess found drowning in it far more pleasurable.

Rory's editorship made everything better and worse. Better, in that he _knew_ this was by far the best thing he had ever written. She had a knack for noticing the natural connections in his work before he did, stringing together characters and sketching parallel plot points in the far reaching corners of his universe. When he became stumped by a scene, or irritated by an inconsistency, she'd list out six different suggestions, each better than the last, enabling him to skip past his usual angry nights of writer's block and whiskey. His productivity was elevated and escalated, and he often found himself lost in the narrow handwriting that she scribbled in the margins and in the line spaces. He learned quickly to print his chapters single-sided and double-spaced. It was a waste of paper, but more often than not she would end up flipping the page and writing on the back, slanted, hurried, caught up in her own excitement. Jess never resented a single word. And when he reached the end of one of her edited chapters (always capped by a near essay-length review and a bullet pointed list of a dozen or so questions) he always felt a sense of emptiness, of loneliness. That drive, to get more of her feedback and to see her handwriting again, kept him up late into the night, typing and rewriting and stretching his talent as far as it could go.

It was worse because he knew he was being a crap worker at the publishing house, and because somehow it was already Christmas and he had no idea where the last couple months had gone. He'd imagined himself suspended in time, but time it turned out continued to move even if Jess paid no attention to it.

He had spent Thanksgiving with TJ and Liz, god help him, but decided to go to Stars Hollow for Christmas to be with Luke. He was rather looking forward to it. Back in November, a few days before Thanksgiving, Rory had called him while she waited for her train to Connecticut. "Will I see you this week?"

He told her no, unfortunately, that he was ethically obligated to spend time with his mother. For a brief moment, or perhaps it was in his imagination, she seemed to be disappointed. But then she quoted Oscar Wilde with impressive indifference. " _After a good dinner one can forgive anybody, even one's own relations_."

"I'm not sure anything as mundane as a meal can make me forgive Liz and TJ," Jess had said, amused. "Especially not a meal that in and of _itself_ requires forgiveness."

Thanksgiving with Liz and TJ always irked Jess. They forced each guest to eat a turkey leg, à la Renaissance festival, and there were always little kids running around jousting. Jess normally had to put up with too many of their festival friends wearing tights and tunics, and although he always appreciated a good glass of wine, he appreciated it much less when he was forced to drink it out of a tankard.

Rory had laughed, and he told her he'd be in Stars Hollow for Christmas.

Now, a few weeks later, he was looking forward to being back in Stars Hollow and seeing her, but Jess was no fool. He was beginning to become wary of the precariousness of this new editing friendship, and checked the locks on that stupid teenage part of his heart that was inextricably and inexplicably bound to her. He figured it was normal - everyone has a first love - and he had done a damn fine job of forgetting his and burying it deep. So far, that part of his heart was quiet, unaffected by the literary kinship that had sprung between them. But Jess was a survivor, prepared and hardened by an abandoned adolescence on the grimy streets of New York City, and he knew how to prepare for a potential storm.

In August, when Matthew and Chris perfunctorily invited him out for happy hour (it was a miracle they still tried considering his steadfast refusal since Em had dumped him) he finally agreed and joined them at some dive place a few blocks away.

They were elated to have him back, and it soon became a familiar habit again. Chris had a girlfriend who would often join them later in the night, after Chris had drank a few too many and was positively delighted to see her, but Matthew was still trying to play the field. Jess would give him endless shit, laughing whenever Matthew acted cocky and received a fake phone number in return. But Matthew had an affinity for poetry and the sweet, approachable look of the harmless boy next door. More than once Jess left him at the bar, still deep in conversation with some pretty former English major, going on about Wordsworth or Kipling or, depending on their historical tendencies, a vivid confessional discussion of Sylvia Plath.

It didn't take long before Jess was back to his reckless ways. It was only too easy, in the dark of a bar, when he had to speak low in her ear to be heard over the music. He was good at reading hints, probably from his practiced years of analyzing people and transcribing their mannerisms and their emotions into characters. He knew when a woman was interested but wanted nothing to do with him - no matter how polished he was now, he could never quite shake the air of trouble that seemed effused in his bloodstream - but he also knew when a woman came to a bar looking for his archetype. One thing would lead to another, and she would pull him outside, whispering in his ear, hands grasping at his until they ended up at one of their places, colliding, searching to feel _something_ in the dark of the night. Mostly Jess enjoyed it, the rush of careless behavior and the heat of passion and intimacy that he always raveled into poetry in the morning. But he kept a careful distance. Once or twice he'd repeat a night, running into her again at a bar, eyebrows raised in recognition, teasing. But more often than not he let the night end and filed it away into his collective of human experience. He wasn't looking for anything serious, but he was looking quite earnestly to forget.

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When he got to the diner, the day before Christmas Eve, Luke was in a ferocious mood. Kirk had set up a Christmas tree selling stand directly in front of the diner, so the windows were blocked by what looked like a thick, encroaching forest. The light inside was dark, tinted green, hazy, and Jess was both claustrophobic and mildly entertained.

"And Taylor won't make him move it because god forbid we block the entrance to the town square and his ridiculous winter carnival," Luke banged the coffee pot into the sink as he tried to rinse it out. " _Why_ is this allowed? Who issues these permits? I swear, if Kirk doesn't move it, he's going to have a pile of woodchips there tomorrow morning."

Kirk stuck his head inside. "I heard that, Luke. That's premeditated criminal intent."

Luke let out a choice string of expletives, revealing a far more sinister premeditated criminal intent, and Jess grinned. He poured himself a cup of coffee from the fresh pot and dropped into a seat at the counter, pulling a notebook and a pen out of his back pocket.

By the time the diner was closing, Jess clued in that the main aspect of Luke's frustration was that somehow, nearly six months after their last Lorelai-related conversation, Luke still hadn't proposed.

" _Why_?" Jess asked, perplexed. It didn't make sense. As far as he was concerned, Lorelai and Luke were married already. The man's life revolved around her, as if she was some fast-talking, over-caffeinated, quick-to-laugh sun. And, always to his surprise, Jess was fond enough of her at this point. He and Lorelai had reached a common understanding years ago on their shared loyalty to Luke, though Jess showed it with sarcasm and Lorelai showed it with an _endless_ stream-of-consciousness joke monologue. Luke's broken leg last year had been the linchpin for Jess, when he saw the true depth of Lorelai's feelings - she was a mess, but a mess that was deeply in love with his uncle - and he'd never doubted her since.

"I just . . ." Luke took off his baseball cap and twisted it in his hands. "I had a plan. I wanted things to be a certain way. But plans never work out, and we've been so busy with the inn remodel, and she made all of these _ridiculous_ My Big Fat Greek Wedding references for weeks leading up to Halloween and then there was the pregnancy scare and - "

Jess choked on his coffee. "Pregnancy scare?"

"No, no, it was Sookie," Luke waved him off, "no way, none of that."

Jess reined his imagination in real quick before he pictured Luke changing diapers and singing lullabies or whatever else grumpy middle-aged fathers did.

"Look," Jess said, firm, "you just have to do it when it feels right. Save your planning for the wedding - I'm sure your plans are great, but that woman is a cyclone and it's almost impossible to hit a moving target."

Luke nodded, eyebrows furrowed in thought, and then continued to clean up the diner, counting the drawer and wiping down appliances.

Jess wasn't expecting Luke to take his advice, let alone act on it two hours later. But as the temperature dropped and the air became colder, Jess began to feel an odd sense of premonition. It was likely just the barometer dropping, but still, Jess could feel the hair on the back of his neck stand up, and he kept looking outside, distracted from his work, frustrated by the pine trees that blocked every window.

When they heard a rise of voices outside, Luke dropped his rag. "You know what . . ." And then he disappeared outside with a bang of the front door.

Exasperated, Jess stood up and walked out of the diner in time to see that it was finally snowing. Light flakes fell in the dark of the evening, layering the boughs of Kirk's Christmas trees and falling in flurries around the gazebo. It was late this year - global warming or god knows what had delayed the snow even after the beginning of December came and went.

Jess saw Luke hurrying across the frosted town square, and, from a distance, recognized Lorelai and Rory standing in the middle of the square with their faces upturned to the sky, revolving slowly, laughing. Luke grabbed Lorelai's hand and dropped to one knee, and Jess watched as Rory clapped her hands to her mouth and jumped up and down.

 _Smooth_ , he thought, shaking his head.

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.

They postponed engagement celebrations for the next night, when Lorelai was due to host Christmas Eve dinner for friends and family anyways. Jess was relieved - he wasn't sure he had enough energy to deal with family and festivities multiple nights in a row. So instead he retreated up to Luke's old apartment with a battered copy of _Lolita_. After a few chapters, uncomfortable and overwrought, he had to go down to the diner and steal a bottle of Luke's whiskey. Lolita sang at the corners of his thoughts and dragged her teeth down the spine of his consciousness. He pushed her away, but let her have him. _We loved each other with a premature love, marked by a fierceness that so often destroys adult lives._

He woke the next day, whiskey on his breath, Lolita whispering in his ear, and couldn't wait for Christmas to be over.

He and Luke showed up dutifully at Lorelai's at five o'clock, each of them wearing some form of blazer and carrying an alcoholic contribution. Luke also brought about six different appetizers, probably specifically to annoy Sookie, but Jess stuck with a tried and true scotch.

Lorelai flung open the door. "Why hello, love of my life and his tagalong vagabond."

Jess rolled his eyes. "Hey, _Auntie._ "

She cringed at that one. Knowing he won the round, he sidled around her - not wanting to witness whatever physical way she greeted her now-fiancée, and made his way to the kitchen.

The house was warm and crowded. He caught glimpses of Rory's grandparents and Jackson and all of the kids, and possibly Lane and a couple of small boys that were banging on a collection of overturned pots and pans. It was very loud. He needed a drink.

Rory was in the kitchen, perched on the counter, chatting with Sookie as the chef tended to a dozen different dishes. Jess met her eyes and gave her a nod. He recognized the scotch glasses in the cabinet above her head, and, feeling reckless, approached her and leaned up against her legs, reaching above and around her for his target. She froze.

Jess backed away, glass in hand, and grinned at her. " _Whoops_ , sorry, thanks."

Rory shot him a reproachful look - "Watch it, dodger" - and returned her attention to Sookie. Jess smiled as he poured himself a short glass of scotch - neat, of course, he wasn't a barbarian - and then glanced up at her to see if she wanted one.

She was holding the narrow stem of a wine glass, but her eyes were on him. She shook her head no when he gestured at the bottle.

"Suit yourself," he shrugged, and capped the bottle.

"I say, what is that?" Rory's grandfather entered the room. He was wearing a suit and tie, elegant as usual, his expression rather jovial. His attention was on the bottle in Jess' hand. "Is that a Lagavulin 16?

"Sure is," Jess swiveled the bottle to show him the label. "Want some?"

"Why, yes I would," Richard said enthusiastically, "thank you. Neat."

Jess obliged. Last time he had shared a drink with Richard had been Thanksgiving at the diner a few years ago, and it had surprised him how much he had enjoyed the experience. Richard handed his dirty glass to Rory, who hopped off the counter to rinse it out. Jess handed him a new glass with a couple inches of the dark, amber liquid.

"Grandpa, you remember Jess right?" Rory asked over her shoulder.

"Of course I do, Rory," Richard smiled as he analyzed the glass, "Jess, the young publisher, Luke's - ah how did Lorelai phrase it - _hooligan_ nephew?"

Jess clinked his glass against Richard's, "Cheers."

"You know Rory, we just had the most marvelous conversation about the publishing business the last time we attended a holiday together. Have you heard about his work at his little shop in, oh, where was it, Boston? Philadelphia? Truly fascinating."

"Yes, Grandpa," Rory grinned, refilling her own wine glass. "I remember. And Jess is a writer too, actually, he's been letting me edit some of his work."

" _Really_?" Richard seemed fascinated. He leaned against the counter, "I enjoy talking to people connected to the literary world. It seems like everyone these days is some kind of _software_ developer or _tech_ entrepreneur, everyone making those _apps_ for your complicated phones. How refreshing to see that you young people are still keeping the literature industry alive. What do you write, Jess?"

"Fiction," Jess replied, "self-indulgent mostly."

"It's great fiction," Rory disagreed, shaking her head. "Along the lines of Hemingway, Grandpa. Jess loves great literature, you can see it all through his work."

"Hemingway would also have liked the Lagavulin 16," Richard sipped his scotch, "my, this is excellent."

"Hemingway liked anything alcoholic," Rory snorted.

Sookie interrupted them, her voice a bit high-pitched. "You guys are great, you know I love an audience, but this kitchen has about ten too many people in it and I can't promise I won't accidentally catch all of you on fire if you insist on standing _that close_ to the stove."

"Oh, sorry Sookie dear," Richard said, his tone hushed. He beckoned to Rory and Jess to follow him back down the hall.

Jess spent the next half an hour before dinner talking to Richard and Rory, his mood lightening, enjoying Richard's portly enthusiasm for literature and scotch and just about anything that wouldn't be out of place in a cigar and billiards room after dinner. Rory and her grandfather were close, as far as he could tell, probably because they were both quite obviously old souls. Jess knew Richard lived for the finer things in life, and valued art and education and all of those things that Jess used to think were for rich snobs. But Rory seemed to run along the same wavelength. Sure, Rory could watch crappy eighties movies with her mom and eat poptarts, but Rory could also live in the nineteenth century, absorbed in Austen, hands wrapped around a cup of tea. And Jess, finally at a place in his life where he could mention an artist like Dickinson or Bronte without pretending to scoff and be an icon of the proletariat revolution, found it easy to drink scotch and banter with the pair of them.

Before long Sookie banged a wooden spoon on a pot and announced that it was time for dinner. They had set up a mismatched collection of tables to create one long table, set with a random assortment of cutlery and groaning under the weight of Christmas food. Jess saw Luke's contribution tucked at the end behind the wine bottles, as if to hide it. He hid a grin. Luke's devilled eggs and bacon brussels sprouts did look a bit out of place compared to the obviously fancy and beautifully plated platters of food that Sookie had prepared. Lorelai lit a few long candles and ushered everyone to seats, careful to guide the gaggle of kids to their own fancy little set up at the coffee table and ignoring Emily's horror at the general miscellany of the table - "Do you even own a matching china set, Lorelai?"

Jess found himself at the end of the table, near Richard and Lorelai. Rory was settled on the other end, next to her grandmother. When Jess scanned the table, he caught her looking at him.

"Lorelai, this young hooligan is really quite impressive," Richard told her, "He's been published already - Rory said the New York Times reviewed his last book!"

Lorelai passed him the scalloped potatoes. "Yes Dad, the young hooligan has really grown out of his days of teenage angst and vandalism. That's why he's allowed in the house these days, see. We're not so worried anymore that he'll pillage and plunder and blow the house down."

Jess snorted. He filled his wine glass with the cabernet that was making its way down the table, and topped of Lorelai's glass too.

"No really, Lorelai, I just think it's remarkable," Richard continued. "And to think that Rory is editing his next book! This could be break she's looking for."

Lorelai shot them both a look as she cut her meat. "Rory's editing your book?"

"Yep," Jess said, glancing at the other end of the table where Rory was chatting with Lane. "Or trying to anyways, it's a load of crap."

Richard ignored his comment, much like Rory would have done. "Nonsense, if he's been reviewed by the Times, I'm sure it's quite good."

"I'm sure it's better if Rory's editing it," Lorelai seemed as though she was trying to sound casual. "How long as this been going on for? Don't you have a different editor anyways, Jess, being the fancy published author you are these days?"

"I do have another editor, yeah," Jess said, keeping his tone light. "She's on maternity leave now though, and it never hurts to get a second opinion."

Most of what he said was true. His editor was on maternity leave, not that it really mattered when his work was unfinished and he had no upcoming deadlines. And it didn't _hurt_ Jess to have a second opinion on his work. But he wasn't sure his editor would be thrilled at his current arrangement if she knew about it.

He felt Rory's eyes on him again, and knew that she must have heard her name once or twice and was curious about the subject of the conversation. But the table was loud and he didn't make eye contact.

"Have you read any of his work, Lorelai?" Richard asked, perfectly happy to continue the topic, even though Jess was more than ready to get the spotlight off of him and his melodramatic literary career.

"No, I leave that whole 'reading' fad to Rory mostly," Lorelai shrugged. "And I feel like Jess and I would have fundamental disagreements about how much angst and sarcasm are overkill."

Jess chuckled. "Probably."

"But anyways, Dad, what was Mom telling me about you two going to Europe again?" Lorelai deftly changed the subject. "When is that happening?"

Jess appreciated the change in conversation, and listened to Richard explain his plans to sail the Danube and visit the great institutions of western civilization. But Jess knew that Lorelai changed the subject on purpose, and wondered absently why Rory hadn't told her mother about their editing partnership. Although, now that he thought about it, he hadn't exactly updated Luke on the situation either. It didn't feel like it mattered that much. Rory edited Jess' work in the same way that Jess came down to the diner to help Luke install a new shelving unit - people did favors for each other.

He knew, though he did his best not to think about it consciously, that Rory's editing probably meant more to him than the shelving unit did for Luke. But he felt Lolita tugging at him once more. _Look, at this tangle of thorns_ , she whispered, but Jess pushed her away, focusing intently on the conversation.

The group ate their way steadily through the food. Jess could hear holiday music from old school Hollywood Christmas specials playing cheerfully in the background, and drank his wine to stifle his usual distaste for holiday stereotypes. But sitting with Lorelai and Richard was, as always, more pleasant than he expected. Before long Lorelai was teasing both of them, throwing rapid-fire references that Jess - usually fluent in Gilmore, thanks to years of practice - caught only most of. He retorted skillfully enough, sticking to his usual specialty of short, sarcastic rebuttals, but found the flow of conversation gratifying enough to prevent him from switching back to scotch. Richard just chuckled and purposefully ignored Lorelai's jokes - he seemed to have years of practice of doing just that - and tried next to engage Jess in a conversation about the southern bourbon trail.

When the dinner plates were clear, and Sookie began threatening to bring out dessert, Lorelai waved her hands to get everyone's attention. "Hey - hey!"

Jess leaned back in his chair, looking up at her.

When everyone was quiet, Lorelai stopped waving and flipped her left hand, showing the sparkle of the engagement ring that Luke had held on to for so damn long. "Luke and I just wanted to say how grateful we are for all of your support and for showing up tonight for Christmas Eve, even knowing that you'd be roped in to celebrating an engagement too. We know you all _meant_ to just have to deal with a holiday tonight, but we're shamelessly taking advantage of this to celebrate us too."

Sookie snorted. "It's about time!"

"It _is_ about time," Emily Gilmore agreed, her tone stern. Amused, Jess saw his uncle look determinedly in any direction that wasn't Emily's.

"Thanks, Mom," Lorelai raised her glass, rolling her eyes, "so, happy Christmas Eve - or solstice or any pagan event you choose to celebrate on this night of great food and drink - and to boring married years to come!"

Rory cheered, "Here, here!"

The table applauded. Jess leaned over, reaching behind Lorelai, and clapped Luke on the shoulder. His uncle seemed embarrassed by his own happiness.

The conversation dissolved into well-wishing, and Jess stood to begin clearing dinner plates. He gave Luke enough crap about all of this, he didn't need to listen to Sookie plan the wedding menu and Emily recommend a florist. Hell, he knew Luke didn't care about any of it, as long as it made Lorelai happy. Jess disappeared alone down the hallway, hands gripping a stack of plates.

Rory caught up with him in the kitchen, her hands full of cutlery. "I think, if you're not careful, Grandpa might try to adopt you. Or induct you into his bridge club."

"Bridge, huh?" Jess set the dishes in the sink and leaned back against the counter, hooking his thumbs in his pockets. "Can't say I'd benefit him much there, but I'd be a great sport for after-dinner cigars."

"I'm sure he'll offer you one as soon as dessert is done," Rory shook her head.

Jess smiled. He watched as Rory rinsed the cutlery in the sink, throwing handfuls in the dishwasher. She was wearing black jeans and some kind of maroon sweater, her hair pulled loosely in a dark, silky ponytail. She already seemed lighter since he'd since her last, the familiar spunk and that he was accustomed to returning in the relaxed tilt of her shoulders.

She turned to face him, wiping her hands on her jeans. "Do you have another chapter for me soon?"

"Art takes time, Gilmore," he said. "I can't just write to please you."

That was possibly a lie. He was writing faster than he ever had, late into the night, consumed, nearly-but-not-quite desperate to send his work so that he could receive a quick reply. She was as integral a part of his writing process as coffee or his laptop - if he wrote for anything, it was for the narcissistic catharsis of feedback.

 _Her feedback_ , Lolita hissed and bit his earlobe, but Jess ignored her. _Years of secret suffering had taught me superhuman self-control_.

Rory's eyes narrowed, a smile tugging at the corners of her lips. "You're supposed to make your readers happy, Jess."

He shrugged. "My readers are never happy. They have to read my work."

"Not true," she contradicted, "I'm happy."

He kept his face blank, but he felt an internal twist, somewhere deep behind his abdomen. When she said _I'm happy_ her bright eyes had that dance to them, the spark that had hooked him _hard_ when he was a teenager. She was playing with sparks, throwing them up in handfuls. And he saw her body language, saw the way she leaned slightly towards him, her eyes dancing, and, if he wasn't a cynic or a nihilist or an idiot, he knew that if she was another woman looking at him like that in the dark of a bar, she wanted him.

Dangerous thoughts. Lolita was pissing him off. _I broke her spell by incarnating her in another._

Jess shrugged again, but he watched her, guarded. "I should have another one for you later this week."

"Great," she flashed him a bright smile. "Feed your addict."

"Again - if you want something worth more than the back of a cereal box, you're just going to have to be patient."

"Readers aren't patient, _Jess_."

They returned to the other room, bantering, but Jess felt himself unconsciously drifting further away from her, brushing the wall. He was wary.

The room was bright, full of laughter. Emily and Sookie had decided to ignore Lorelai completely and were sketching out wedding plans on the back of magazines. Lane high-fived Lorelai, who was leaning against Luke's chair as she chatted with Jackson about how many family members are appropriate to not invite to a wedding. Rory heaved a happy sigh.

She swiveled to face him. "What are you reading right now?"

"Nothing," Jess lied. He was smooth enough to be convincing - he was not going to say that Lolita was tracing her name on the small of his back.

" _Why_?"

"Because I have an editor that is driving me up the wall," he retorted. "The normal writing process isn't quick enough for her. I have no time to read - just writing and writing, day and night, chained to my computer, a slave to her need for material."

Rory laughed. "I don't believe that for a second . . ." She continued talking, but Jess was distracted.

At the far end of the table, where Jess had been seated earlier, Richard half rose out of his chair. He looked confused, concerned. His hand rose to his chest, clutching at his dress shirt, scrabbling at the fabric.

Jess felt himself tense. The noise in the room seemed to fall away.

"Jess?" Rory's voice swam to him.

Richard lost his grip on the arm of his chair and fell forward, hands gripping the table, head bent.

Rory whipped around, following Jess' eyes, in time to see Richard collapse onto the floor, the sound of the scotch glass shattering causing a sudden silence in the room.

" _Grandpa_!"

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 _And the rest is rust and stardust_ , Lolita murmured.

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* * *

Apologies for mixing _Lolita_ and Christmas - but I doubt Jess would care.

Thank you for your amazing feedback! Your reviews have made me smile so much.


	8. Chapter 8: Valentine's Day 2011

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 **Chapter 8**

 **Valentine's Day, 2011**

The Valentine's decorations in the hospital were drab and halfhearted. Red cut out hearts were taped haphazardly to the walls, and a bunch of partially deflated red and pink balloons bobbed wearily at the nurse's desk. Rory wrinkled her nose at all of it with distaste. She was no fan of Hallmark holidays, particularly in such a sterile, perfunctory setting. Nurses bore cupid pins and heart barrettes in the way that mall employees begrudgingly wore Santa hats during the holidays - another thing to do, another week to pass.

She was in New York, at a hospital uptown. Her grandpa had been moved there shortly after his Christmas Eve heart attack to be under the care and supervision of a renowned heart specialist. (Emily, of course, had insisted on only the _best_ medical professionals.) After nearly two long months Rory was used to the hospital, with its motel watercolor art and waiting room chairs upholstered in scratchy, generic prints. She had even gotten used to the coffee, which was admittedly terrible, even though she had the option of braving the icy New York winter and walking a few blocks to a nearby coffee shop.

Rory avoided thinking about the night that it had happened because it made her heart clench and her palms sweat. But sometimes, when she dozed off in the chair in her grandpa's room, she'd be jerked awake by nurses running a stretcher outside the hall, or the far off sounds of sirens bringing in new patients and new emergencies, and it would all come flooding back to her.

She remembered the look on Jess' face, and how she turned around with her heart in her throat. Richard fell in the span of half a heartbeat, but it felt like it lasted ages.

Then, everyone had started shouting at once. Emily had screamed and hurried around the table to where Richard lay, followed quickly by Luke and Lorelai. Lane, who was always the godsend of common sense, reached immediately for the phone to call 911. Jackson darted to shepherd the kids upstairs. And Rory had just stood there, mouth open, rooted to the floor, shock coursing through her. It wasn't until Jess gently grasped her shoulders, to move her to one side so that he could get by her to help Luke move the table, that she realized time was still ticking.

The night had been a long one. The ambulance rushed Richard to the nearest Connecticut hospital, but by morning he was being airlifted to Hartford. Rory stayed curled up in a hospital waiting room chair, wide-eyed, as the night dragged on and they waited for news. Luke tried to calm both Lorelai and Emily - an impossible task - and eventually just gave up and let the two women wring their hands and harass every hospital employee that had the misfortune to walk by.

In the early hours of Christmas morning, when the sky was beginning to lighten, snowflakes whirling against the glass, Jess appeared silently in the waiting room. He handed each of them a large, steaming coffee, placed a box of pastries on the low table in front of them, and settled inconspicuously into the chair next to Rory, pulling a battered book from his back pocket. She had wrapped her fingers around the hot coffee and closed her eyes.

It those first few days, when the doctors spoke in cautious platitudes and wary statistics, Rory felt oddly disconnected to reality. It was lucky, really, that it happened over the holiday break because she didn't remember that she had a tutoring job to tend to until a week later, when Richard was being transferred to New York anyways. In the Hartford hospital Rory alternately let her mother jabber her ear off - Lorelai never handled hospitals or emergencies very well - and sat quietly next to her grandmother, who was very stoic except for occasionally snapping off demands to hospital staff. They could go in and see Richard, after a while, but he stayed in a deep slumber.

When the transfer to New York happened, Emily promptly reserved a long term hotel room uptown. Lorelai, however, couldn't leave the inn for too long and couldn't afford to stay in the city. The three Gilmore women resolved to reinstate Friday night dinners, though 'dinner' really meant sharing a take-out vigil in Richard's hospital room and then Lorelai sleeping on the pull out couch in Emily's hotel room before returning to Stars Hollow the next morning. Every once in a while Luke came along, and then drove Lorelai home in the dark late hours of the night.

So it went, as the weeks dragged through January, and then February. It was a bitter, icy winter, and Rory felt uncomfortable with the normalcy of it all. She would go to tutoring appointments on the Upper East Side and then drop by the hospital, as casually as she would stop to pick up milk or return a book to the library. Her grandmother was nearly always there, and they would sit and talk for a few minutes, or Rory would read while Emily continued to run Hartford's aristocratic social scene through long, scolding phone calls. The pattern began to feel natural, although Rory would sometimes glance at her grandfather, peaceful in his bed, and feel a pang of sadness at the absence of his booming laugh. The room felt smaller without him in it.

She picked up _Anna Karenina_ , because something about winter and sadness reminded her of Tolstoy and his tragedies. The wintry Russian landscapes, which turned to spring and summer and back to ice once more, wrapped her alternatively in anguish and frivolity.

 _There are no conditions to which a person cannot grow accustomed, especially if he sees that everyone around him lives in the same way_. Rory quite agreed.

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On the Friday afternoon after Valentine's Day, Rory found herself alone in the hospital waiting room with Anna Karenina. It was 3pm. She sighed, and checked her phone.

A fierce blizzard raged outside, the winds howling against the towering hospital building. According to the news reports, it was a "historic storm." The nor'easter had begun threatening the city in the morning, the wind screeching down the Hudson and flying down the wind tunnels that stretched down the avenues. By late morning it was snowing in thick, blinding swirls, and at noon the city shut down the subways and ordered its millions of residents to take shelter and to please _not_ call restaurants for delivery.

Rory, whether she liked it or not, was stuck in Manhattan. She had an Upper East Side tutoring appointment in the morning, and had stuck around for Friday night dinner. But with the tunnels closed, the subways shut down, and the roads blocked by snow plows, there was no way she was getting to Brooklyn anytime soon.

Her phone rang. It was Lorelai. "Hey mom."

"Hey kid," Lorelai sounded harried and exhausted, "I got as far as Milford, but I don't think they're going to let me go any further. They've blocked off the highway. I think Connecticut might be calling it a state wide emergency."

"It's just a little snow," Rory protested. "Come on, where's that famous Connecticut grit? It's like the wild west in Milford, practically."

Lorelai snorted. "They seem to have lost all their spunk. The traffic cops are wearing _mittens_. I'm half expecting them to start handing out hot chocolate to all of us stranded drivers."

"Are you stranded?" Rory asked. She felt a twinge of concern.

"No, it takes more than a little snow to strand a jeep," Lorelai said. Rory imagined her patting the steering wheel fondly. "I'll make it back to Stars Hollow okay, but I can't make Friday night dinner kid. I'm so sorry, you're going to be stuck with Grandma."

"Grandma can't make it either," Rory said gloomily, "She went back to Hartford for a charity event last night and the airport won't even let her congressman friend fly her here on his private plane."

"Are you _kidding_ me?" Lorelai said with mock outrage. "The state is such a pansy that they've shut down _private planes_? How are the rich and powerful going to travel? Who do they think they are, not allowing Connecticut pseudo celebrities to fly in hurricane-force winds?"

"I know," Rory agreed, "it's a travesty. A true violation of personal and privileged freedom."

"Emily Gilmore will not stand for this," Lorelai said, "there will be _complaints_. And an _inquiry_. And maybe a yelp review."

"A yelp review for the airport? Or the state? Or the Governor?"

"For all of it," Lorelai said decisively. "Unconscionable. Jeeps can't have access to the road and planes can't have access to the sky. What is the world coming to?"

"It's a mess," Rory glanced at the window. "I'm stuck in Manhattan alone now."

"You can't get back to your apartment?" Lorelai's tone immediately shifted to one of concern.

Rory kept her voice light. "They shut down the subway and the tunnels. I might be able to bribe a cab driver, but I'm not too optimistic. Currently planning on sleeping on the chair in Grandpa's room."

"You're at the hospital now?" Lorelai sounded relieved, "Oh good. If I want my kid to be anywhere during a state emergency, it's preemptively at the hospital. "

"I don't want to sleep here," Rory said, annoyed.

"Ah, you'll be fine," Lorelai shrugged her off. "Keep Dad company, tell him how terrible me and Mom are for not coming to visit during a crisis."

"Will do."

"Oh, and actually," Lorelai paused. Rory could hear her turn signal blinking. Lorelai swore and fumbled the phone. " _Crap_ , sorry, trying to turn around this is a mess. Anyways, I think Jess is in the city too."

"Jess is here?" Rory felt her voice get higher. She frowned and pulled on a stray thread on her sweater sleeve.

"Yeah some book signing or conference or Barnes and Noble fight club, I don't know what hotshot authors do," Lorelai fumbled the phone again and swore. "Alright kid, I gotta go, I feel like a cop is about to yell at me for talking and driving in hazardous conditions."

"You are probably a hazard right now," Rory nodded.

"Goodbye, love you, be safe, let me know if you end up faking sick to snag a hospital bed to sleep on - I'm not paying the insurance deductible, but if you make up a fake identity, I won't be mad."

"Bye," Rory laughed, "drive safe. Let me know when you're home."

Lorelai blew her a kiss through the phone.

Rory hit _end_ and then stared at her phone, cradled in her hands. She was alone and stranded in a blizzard in Manhattan. Her grandfather wasn't very good company at the moment. And apparently, Jess was buried on the snow-covered island with her.

She exhaled, eyes unfocused. Jess had been on her mind a lot lately. Rory didn't like to think about it all that much, or acknowledge it at all really, because she felt enormously guilty whenever she was sitting vigil at her grandfather's bedside and her thoughts wandered unaccountably and repeatedly to Jess.

Perhaps it was Tolstoy's fault - Anna Karenina was certainly never one to shy away from her own internal drama. Or maybe it was Jess' fault. More specifically, his damn book's fault.

He continued to send her chapters, and she still consumed them like a wildfire, like a madness, like an addict. Jess had always been a bit old school, a man who appreciated such antiquated things as record players and printed books and the romanticism of the post office, so he mailed them to her, manila envelopes thick with the musings and rantings of a talented poet. Sometimes he would send her a one-word text when he dropped one in the mailbox - _incoming_ \- and she would wait impatiently for the couple days it took to show up crammed in her mail slot at her Brooklyn apartment. Worst were the days when she was heading to work, or to the hospital, and she couldn't immediately hurry to one of her favorite bars or coffee shops to rip the thing open.

But there was no greater feeling then getting home at the end of a long day and finding an envelope with her name on it in his small, slanted scrawl. Rory usually dropped her tutoring books, grabbed her coat, and flew to the pub on her street. She'd tuck herself into a corner of the bar, order a whiskey because nothing else felt appropriate for Jess Mariano's work, and let herself dissolve into the tortured, tender contours of his novel. She wrote lines upon lines of hastily scribbled notes, gently pulling apart the strands of his work, questioning, fixating, speculating, and suggesting. It felt like a high - like the greatest possible rush. And when she reached the last page, and felt her heart nearly yanking itself to pieces for more, she tended to order another whiskey and firmly tell herself not to call him.

Rory liked to tell herself that this was why she couldn't keep her mind off of Jess, because he was the literary heroin dealer to her hopeless addict. But Tolstoy raised his eyebrows at her. _Rummaging in our souls, we often dig up something that ought to have lain there unnoticed_.

She hesitated, thinking, listening to the wind howl. The windows in the waiting room were completely white, blown out with snow.

Her natural instinct to rationalize kicked in, and the familiar stream of moments and memories blossomed in her mind. Maybe it all started with the first manuscript Jess had let her edit. But even then, she had been able to separate the man and the literature. Jess was Jess - a problematic, probably unresolved ex boyfriend that she had long ago resigned to the archives of her history. But Jess was also an author that twisted her heart strings around his fist and _pulled_ , twisting, drawing her deeper into the recesses of her heart and her mind that she usually skimmed over. Those were dark waters, full of heartbreak and teenage anguish and guilt.

She remembered him on Halloween, his calm confidence, removed and recovered from the storm of depression he had faced after his cheating ex. Something deep in her abdomen felt tight. Rory, despite her calm, logical insistence that she was _only_ attracted to Jess' literature, was beginning to suspect that there might be something more. Those dark waters that concealed her Jess baggage roiled, restless.

Tolstoy tended to make her musings worse. _Sometimes she did not know what she feared, what she desired: whether she feared or desired what had been or what would be, and precisely what she desired, she did not know_.

Against her will she remembered the sharp line of his jaw, the way he carelessly rolled his sleeves up his forearms, those dark, inscrutable eyes that observed the world with detached curiosity. Sometimes, unbidden, she would flash back to her seventeen-year-old self, breathless as he pressed his body against hers outside of Luke's diner late at night. She remembered laughing, giggling, even as his lips blazed against her neck, occasionally nipping her with exasperation at her inability to handle it seriously. But she couldn't handle it then. She could never handle Jess - he _burned_ with passion, with desperation, with a raw yearning for connection that she now recognized in the lines of his prose. And back then, at seventeen, it was all she could do to grasp his hands and kiss him back, trying to communicate as fiercely as she could that she _got it_ , she understood, she felt the depths within him and wanted to do everything she could to be enough, to fill his soul.

Rory sighed and rubbed her eyes. These were dark and dangerous thoughts, and it was all entirely unhelpful anyway. Best she could tell, Jess didn't think about her at all except to appreciate her editing. All of her wandering and rationalizing thoughts of Jess - when she should be worrying for her grandfather, or trying to find a career - were confusing and pointless.

But at the same time, they were both in the city, and it was a historic storm, and Rory couldn't really think of a reason why she _shouldn't_ text him. They were old friends, after all. And they talked regularly, if occasional book recommendations and pages of literary correspondence every week counted as talking.

Rory looked down at her phone. It was turning into a bad habit, spontaneously springing herself on Jess. This would make it one too many times in a row that she texted him to meet her out of the blue, or just showed up. But - she felt her abdomen squeeze a little tighter - he always said yes.

Ignoring both her reasonable instincts and the gossiping giggles of Tolstoy's nineteenth century Russian ladies, she picked up her phone and typed Jess a quick text. _I hear you're also stranded in Manhattan_?

Before she could set her phone down, it buzzed with Jess' response. _Correct._

Rory glanced at the harried nurse at the counter. She felt her heart beating a little more quickly. She plowed ahead anyways. _I'm on the UES. Care to join me?_

This time his response took longer. She chewed on one of her nails and watched the exhausted balloons sink a little closer to the desk. Maybe this would be the time he said no, that he was busy, that it would be idiotic and dangerous to go out in this weather.

But after a few, long, ambiguous minutes, her phone vibrated. _Sure. Are you at the hospital_?

Rory smiled and typed back, _Yes_.

She waited a moment, and then set her phone on the armrest of her chair and reached into her bag to pull out _Anna Karenina_. She didn't expect Jess to respond, or say when he would get there, or how far away he was. He was never one to communicate when he could leave people in suspense instead.

Tolstoy teased her immediately. _It's like scarlet fever: one has to get it over_.

Maybe that was what was wrong with her, Rory mused. Scarlet fever.

She left the book open but felt her eyes glazing, surrendering to her idling, stream-of-consciousness thoughts once more. It wasn't that she hadn't been trying to live a life outside of being Jess' editor - she enjoyed her job and her students, she made a habit of applying to a job or two every week, she spent hours at the hospital caring for her grandmother. After Lorelai had nearly collapsed with laughter on hearing how long it had been since Rory had been on a date, she even tried to meet a guy or two, finally accepting her cute barista's offer to "grab a drink some time." Predictably, it had been boring. Or maybe she had been boring. Jess' latest manuscript arrived as she was heading out the door to meet barista boy at the bar, and she'd spent nearly the entire night with the unread chapter tantalizing her in the back of her mind. After the third time that she forgot what they were talking about, he had smiled in that pained sort of way and offered to walk her home.

Although that date had been a fiasco - and Rory now felt she could never go into that coffee shop ever again - she had since recovered her dating reputation. On Valentine's Day, earlier in the week, Rory had been curled up on a bar stool, reading Jess' most recent chapter, when a handsome Brooklyn guy with square glasses sat next to her and asked lightly if she ever snapped her pen in half from writing so hard.

It was fortunate for him, really, that Rory had just finished editing and was in that aching, moody place that made her want to be reckless and call Jess and demand more. She laughed, let the Brooklyn guy buy her a drink, and found herself rather charmed. She invited him up to her apartment to watch a movie - something indie and hipster that he said did great at Sundance - and felt rather proud of herself when they ended up kissing on the couch. Rory was never one to be _too_ reckless though. When the credits rolled she hit the brakes and said that she had an early tutoring job the next morning and needed to get to bed. He flashed her a grin and wrote his phone number on a crumpled receipt in his wallet before bundling into his coat and disappearing into the cold night.

Lorelai didn't believe Rory when she told her about it. "Daughter, you made it up. It was Valentine's Day. No lonely woman ever meets a halfway decent guy alone at a bar on Valentine's Day. Maybe you even dreamed it! I heard those drugstore assorted chocolates can have dangerous hallucinogens. And those candy hearts might not even be approved by the FDA . . ." But when Rory texted her a photo of the receipt - and a screenshot of the ensuing text - Lorelai begrudgingly gave her credit for manifesting a lonely hearts impossibility on February 14th.

Rory was tangentially proud of her own nerve - she was in her twenties after all, it was about time she picked up guys at bars - but she couldn't say she cared at all about Brooklyn guy. If she thought about him, she eventually ended up returning her mind to Jess, and by the time she started remembering her aching teenage self, she would push all thoughts determinedly out of her mind.

One of the alarms went off at the nursing station, startling Rory from her reverie. The nurse sighed and hurried off towards whichever patient pressed a call button.

She shook her head, firmly, as if to clear her mind of all the treacherous directions it was intent on going. Instead, she forced herself to read. Sentence by sentence, she slowly forgot her own priorities, and lost herself somewhere on a train in the Russian countryside.

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A hand gently pulled Rory's book out of her hands. She started, and looked up, her shock melting into a smile when she saw Jess, eyebrows crinkled as he read the title. He looked windswept and frostbitten, his coat covered in snow, a wet beanie pulled low over his ears.

"Anna, really?"

Rory shrugged. " _All happy families are alike; each unhappy family is unhappy in its own way_."

"Anna because of the family drama?" He glanced around at the hospital waiting room.

She half shrugged. "Family drama. Blizzards. A healthy dose of obsessing and whining over love and happiness."

Jess handed the book back to her. "You know I love obsessing over love and happiness."

Rory laughed. "No, you don't."

"Not with other people," he amended. "But to my keyboard, sure. Tolstoy isn't a leap from Hemingway. Just a little less gritty."

She supposed the comparison wasn't too far off. "Alright, fair." She put her book back in her bag and stood up, grabbing the pile of her coats and scarves that she had tossed in the chair beside her.

"Where are we going?" Jess looked at the window, wary. "It's hell out there." His coat was already dripping water on the floor.

"I know a place," she winked.

She led him to the elevator, and took it a few flights down. Jess snorted when they entered the hospital cafeteria. It was nearly empty - apparently the hospital didn't get many visitors when the city shut down - and looked even more depressing than usual without the usual clumps of chatty interns in scrubs and families poking doubtfully at trays of gray food. The room was dimmer than usual with the snow built up against the windows.

"I might prefer the storm," Jess said honestly, standing in the doorway and looking at the cafeteria with heavy skepticism.

"Oh trust me, I'm a regular." Rory led him to the far counter where a thirty year old coffee maker steamed in a forlorn sort of way. She poured each of them a styrofoam cup of bitter, black coffee and then led Jess to a table by the window.

They set their things down across from each other. Rory held the cup, enjoying the warmth in her fingers, and watched as Jess unbuttoned his coat and laid it out over a nearby table to try to dry out. He pulled off his hat and shook his head, wet droplets flying. "I don't really recommend it out there right now," he said casually.

"You don't say?" Rory said, amused. He sat across from her, and she pushed his coffee towards him.

Jess tasted it and wrinkled his nose. "This is what you drink now?"

"Well, it's here and it's free."

"And you're _Rory Gilmore_. Didn't your mother have you shooting espresso as soon as you could eat solid foods?"

"Before, actually. Coffee's a liquid, it comes before solid foods."

"And you're drinking _this_?" Jess peered into his cup.

Rory grinned. "Beggars can't be choosers. Caffeine is an addictive substance, you know. I'll get a fix wherever I can take it." Internally, she recognized that her words probably held a dual meaning, but she chose to ignore that particular sidebar.

" _Be bad, but at least don't be a liar, a deceiver!_ " Jess quoted Tolstoy. "There is no way this is okay with you."

"Well . . . no," Rory surrendered. "But the last part was no lie. I take what I can get. And last I checked, it's a statewide emergency, I'm assuming coffee shops are closed."

Jess nodded. "Everything but churches and liquor stores. The essentials."

Rory hummed appreciatively and sipped her coffee. Jess was still trying to get one of his frozen gloves off. She noticed a few snowflakes caught in his dark eyelashes, and then immediately tried to un-notice them.

"So to recap, your plan, in getting me to come meet you, was to hang out in a hospital cafeteria and choke on bad coffee while we wait for the glaciers to move down Fifth Avenue and block our routes home?"

"My route home is already blocked," Rory pointed out. "You want to try to get across the river right now?"

"Not really," Jess said. He reached for his bulky backpack. "You're lucky I came prepared."

Rory watched, delighted, as he pulled out take out containers of Thai food. When he reached in for napkins and utensils, she saw the glint of what may have been a wine bottle too. He offered her a pair of chopsticks. "Have at it."

"Have I mentioned, lately, that you're wonderful?" She opened a container of green coconut curry, and nearly whined in appreciation at the rich, spicy scents that overpowered the cafeteria's usual odor of greasy fries and antiseptics and bitter coffee. She could have melted with gratitude.

"Not lately, no, but as a chronic narcissist I'm always glad to hear it."

"You're _wonderful_ ," she said emphatically. Another container was filled with spicy beef and noodles, and a third held spring rolls. "a hero among mortal men. How did you find this? I thought everywhere was closed."

"The Thai place below my friend's apartment was about to close but I sweet talked them into giving me whatever they had left," Jess unwrapped his chopsticks.

"You're staying with a friend?"

Jess nodded. He didn't elaborate. For a brief second, Rory felt what may have been a small twinge of curiosity coupled with a dash of jealousy.

"I also happen to have a fold out couch," she offered, conversationally, "you're welcome to it whenever you need a place to crash for your fancy New York author events."

He tipped his shoulders. "Might take you up on that some day. My friend's place is a little too . . . Woodstock for my taste."

Rory laughed, "Come on, Jess, embrace the Woodstock. Release your inner flower child." She took a bite out of a spring roll. "Wow, this is good."

"My 'inner flower child?'" Jess raised his eyebrows at her, disgusted. Rory grinned.

They continued bantering, steadily working their way through enough Thai food to probably satisfy a family of six. Jess gave her a usual amount of grief for eating like her life depended on it, but Rory just gestured outside and said she may as well pack on the calories in case they were trapped sheltering from the arctic tundra for weeks.

The conversation flowed easily, naturally, as the window grew darker and colder. The storm seemed to get worse as night gathered upon the city. The wind shrieked as it barreled around the skyscrapers, slamming gusts of snow against the windows of the dingy cafeteria. Every once in a while Jess or Rory would glance at the window, concerned when a particularly fierce blast threatened to crack the glass. But, when the structural integrity of the building seemed to recover, they would return to their dialogue, building on their flow of references and jokes and comments.

Rory felt as if she was becoming unzipped in two. One part of her - the rational, logical, valedictorian, careful, bullet pointed list side - enjoyed the conversation with an old friend but stayed back, relaxed in her seat, keeping her attention focused firmly on the topic at hand. But that other part of her - the part that didn't seem to give a damn about what she _wanted_ to focus on, the part that focused on everything treasonous and couldn't keep herself from looking at Jess - wanted to learn forward, ask mischievous questions, draw the conversation down those dark, flirtatious roads that always lead to a more fun type of banter.

 _What_ was wrong with her? Rory shook her head again, like she was trying to forget something.

Jess paused mid sentence, amused. "You okay?"

"Sorry," she felt heat rise in her cheeks. "Lost my thoughts for a second there."

"Need to get your head checked out? We are at a hospital right now," he suggested.

She laughed weakly. "No, I'm good."

He dropped his smile and examined her in that familiar, uncomfortable way, like he was evaluating her. "How's Richard doing?"

Rory's cheeks burned a little brighter. Her grandfather would have been a much more appropriate and respectable subject for her wandering mind. "Uh, no progress. They're optimistic, but they say we just have to be patient, wait it out while his body heals itself."

Jess seemed to contemplate this. "I'm sorry," he said, after a pause, "I really like him. Man has his priorities straight."

Rory appreciated his use of the present tense. She caught herself, sometimes, using past-tense verbs, and always jerked with shock and horror when she noticed it.

"He'll wake up soon," she said, more or less confidently. "He's too stubborn not to. And besides, my grandmother will kill him if he doesn't."

Jess chuckled, "Not surprising."

Rory watched him. He was looking out the window, which was dark and plastered with snow, apparently lost in thought. She felt that inner twist of her abdomen warm, ever so slightly. She'd never admit it, especially not to Jess, or her nosy mother, but she really loved how Jess and her grandfather always seemed to get along like old friends. That night, on Christmas Eve, she had certainly been thinking all kinds of precarious things about Jess, but watching him effortlessly gain her grandfather's friendship had melted her.

"Do you want to go up and see him?" She offered.

Jess looked at her. His dark eyes were faintly surprised. "Shouldn't it just be family?"

Rory shrugged. "He likes you. And besides, he's used to a crowd of Gilmore women on Friday nights. I'm sure it's far too quiet in there for his tastes."

Jess cracked a smile. "Undoubtedly." He stood and began clearing the empty take out containers.

Smiling to herself, Rory tossed their chopsticks in the trash and gathered her pile of outerwear. She led Jess to the elevator, up a few floors, and through the maze of hallways to a room that felt a bit like her second home at this point.

Rory always knocked, even though she knew no one would tell her to enter. She pushed open the door, "Grandpa?"

The room was silent except for the whirring and occasional beeping of the many machines and monitors. Her grandfather lay in his bed, peaceful in sleep. Tubes and cords tangled around the bed, like a multi-colored web, disappearing under the bed covers and behind the hulking machines. But Richard looked calm, as if he was merely napping in a lawn chair in July in the Hamptons.

Rory assumed her usual perch in one of the chairs by his bed. She watched as Jess stood, his hands clasped behind his back, glancing at the machinery and Richard.

"He looks good," Jess said. His voice was a little lower than usual, affected by the solemnity of the room.

"He does," Rory agreed. "He's gotten some color back. I swear he's gained weight."

Jess chuckled. "Think if I offer him a scotch and a cigar he'll wake up?"

"Maybe," Rory replied, seriously, "when Grandma joked about selling the house I swear he looked angry for two days."

Although he didn't look uncomfortable, Jess still hung back by the door. Rory could tell he didn't want to stay there. She stood. "Waiting room?"

They trooped back to the waiting room. It was completely empty at this point. The nurse's station was dark. Rory knew that late at night the nurse's station on the other side of the building took over for the whole floor.

Jess dropped his stuff on a chair. "Be right back."

She sat in a chair, curling her legs up underneath her. The wind howled and raged against the building. She couldn't see outside through the snow-sealed windows, but she could imagine the thick flurries of snow battering the buildings, the wind whipping the street lights and sculpting story-high drifts against the street corners. The streets would be dark and empty, the city ghostly in the raging storm.

When Jess returned, he held two styrofoam cups. Rory watched, amused, as he pulled the bottle of wine out of his backpack, poured each of them a cup, and returned the bottle to his bag. He was unbothered by hospital protocol. "If the nurses show up, they won't know. And if they know, they won't care."

Rory took her cup. She felt warmth in her entire body, from Thai food or immense gratitude or treacherous thoughts, she didn't know.

"I don't know what I'd do without you," she said. "I mean, actually, I know exactly what I'd be doing without you. I would have had coffee and vending machine snacks for dinner and fallen asleep in this chair reading Anna Karenina, waiting for the hospital generator to go out so I could freeze a slow, painful death."

Jess tapped his cup against hers. "Well, I'd be fine without you, but this is fun too."

Rory laughed. She didn't doubt the truth of his statement.

He pulled Anna Karenina from where she was peeking out of Rory's bag. "Alright Gilmore. Convince me to read this again."

She sipped her wine - Jess had bought some kind of wonderful, dry red that made Rory's mouth tingle and her heart skip a few beats - and then exhaled and quoted Tolstoy. " _I often think that men don't understand what is noble and what is ignorant, though they always talk about it_."

Jess smiled despite himself. He often did that, Rory noticed, when she said something particularly witty or literary or both. She resolved to do that more often.

His retort didn't disappoint. " _God forgive me everything!_ "

"Nice," she appreciated his quote. "But really, Jess, it's a classic."

"A classic that makes me want to throw myself in front of the L train," Jess quipped.

"Oh, _haha_ ," she rolled her eyes. "That was cliché and you know it."

He drank his wine. "That was a cliché. We both know it."

Rory couldn't help herself from grinning. It was like a disease. Her thoughts were perilous, scattered, reaching. His messy dark hair looked so impossibly good.

"But really," Jess continued. "How do you deal with the endless monologues?"

Rory shook her head again - less noticeably this time, she hoped - and launched into a passionate defense of _Anna Karenina_.

They spent at least an hour on Anna. Jess, unsurprisingly, was well-versed in Tolstoy, even as he forced her to defend it. When Rory felt that she had substantially won that battle - when he agreed to re-read her copy as soon as she finished with it - they moved on to Jess' book, which, despite Rory's inner denial, was nearing an end. He seemed a little detached from it, cautious, careful. When she chided him for his reticence, he drained his cup and poured himself another.

"This might be the best thing I've written - credit to you of course," he filled her cup on the _you_ in his sentence. "But I'm worried I'll fuck it up."

"How could you do that?" she demanded.

He shrugged. "I don't trust anything."

Rory rolled her eyes, and this time embarked on a zealous defense of Jess' own work. He laughed and tried to wave her off - "I'm not looking for a confidence boost" - but she ignored him and built her case anyways.

The wind continued to howl and the night grew later. Occasionally a nurse would pass by, shooting displeased looks at their loud conversation and probably suspicious styrofoam cups. But Rory didn't care. She spun higher, enjoying her wine, enjoying being close to Jess, enjoying not resisting the illicit and risky thoughts that threw her headfirst into those dark waters. The later it got, and the more she felt herself irresistibly drawing closer to him, drowning in those waters, the more she knew she was in trouble. If she was unzipped, she had left her rational half down in the cafeteria.

The wine was empty, the room was dark and quiet, and the conversation slowed, languid, easy. Rory was exhausted and pleased. Something about being in a deserted public space in a winter storm made the whole world seem a little disjointed. And lord knew _she_ was disjointed. She gave up on her thoughts. She let them run free. She watched Jess with abandon and let herself say risky, bantering things that her logical half wouldn't have dared let escape her mouth.

After a while, when it was very late and she was resting her head in her hand, listening quietly, she felt herself becoming drowsy. She rubbed her eyes, trying to shake her sleepiness, but Jess saw it. "Tired?" he assessed.

Rory yawned. "A little bit."

He half-smiled and looked out the window. If he was tired, she couldn't tell.

She felt her eyes closing, her body pulling her gently into sleep. She nodded off again. The room was warm and quiet, as the storm howled.

Without thinking about it, without really caring at all what her unzipped rational side would think, she shifted sideways, curling her legs up underneath her, and let her head rest against Jess' shoulder, her eyes closed. She felt him tense a little bit.

The wind shrieked outside. Time felt liquid. He paused, and then shifted her, moving his arm to wrap it around her shoulders, securing her in place.

She cracked her eyes open, just slightly, and saw his right hand flip open her copy of _Anna Karenina_. Despite herself, she smiled as she drifted away.

 _I think that to find out what love is really like, one must first make a mistake and then put it right._

 _._

 _._

 _._

* * *

Thank you to everyone who has left such long, kind, thoughtful reviews! They are such a gift.


	9. Chapter 9: Easter 2011

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 **Chapter 9**

 **Easter, 2011**

On a rainy April evening, when Jess was hurrying back to the publishing house, trying to balance grocery bags and keep the hood of his raincoat up despite the gusting wind, his phone rang. "Damn it," he groaned, and fumbled with his coat pocket, trying to find his phone.

"This is Jess," he answered, his tone short. He nearly dropped a carton of milk on the rain-streaked sidewalk.

"Hey, it's me," Rory said. "Er, are you okay?"

"Yeah," Jess took the stairs up to the publishing house two at a time. He held his phone to his ear with his shoulder and tried to open the door, slipping with the wet keys. "Hang on - " With a deft flick of his wrist, he managed to unlock the door and pushed inside, kicking it shut behind him. "Sorry, just got back home. Give me a second."

Rory waited patiently while he ducked up the stairs to his little apartment, unlocked his door, and flicked the light switch of his kitchen with his elbow. He dropped the bags of groceries on the counter and rubbed his wrists, which he was sure were rubbed raw from the plastic straps.

"Alright," he shrugged out of his raincoat and tossed it on a hook, "what's up, Gilmore?"

He could hear her smile through the phone. "What have you been doing? Storming the fortress?"

"Just about," he kicked off his shoes. "Drawbridge caused a bit of a hassle, but I really showed up the front door with the battering ram."

"Glad to hear it," she was amused, "sorry if I caught you at an inconvenient moment in the battle."

"What's a battle without an extra challenge? Heroes have to persevere through much adversity, last I checked."

"In what universe are you a hero?" she teased. "Black knight, more like."

"I'll take that as a compliment." Jess began putting away the groceries, one-handed. "Battle's won. What's up?"

"I have an interview in Philadelphia this weekend," Rory said, "are you going to be around?"

Jess glanced at the calendar that he had tacked to the wall. "Yeah, I'll be around. What's the interview for?"

"Some publishing house downtown," her tone was casual, but he could hear the underlying excitement. "I guess they do a lot of poetry anthologies, but some longer prose works too."

"Great, you and Matthew can compete over signing melodramatic poets." Jess said sarcastically.

Rory laughed. "I'm not sure I can edit poetry - the lack of rules really bothers me. You free for dinner Friday?"

He leaned against the wall of his kitchen, rubbing his wrist. "I'm supposed to meet up with Matthew and Chris, but you're welcome to join."

"Alright," she sounded pleased, "text me a place and a time?"

"So demanding," he felt himself smirking. "Next thing we know you'll be asking for outrageous things like directions and parking advice. We're really not used to such high expectations here in Philly."

"Too right I will," Rory said, "and you'll be a proper host and respond in a timely and reasonable manner, I'm sure."

"We aim to please," he said dryly.

"I'll see you Friday," she laughed. "Bye, Jess."

"Later," he said. He hung up the phone.

He tossed the phone on the counter and finished putting away the groceries. His apartment was dark because of the storm, the windows deep blue and flecked with raindrops from the gusting wind. Jess always liked spring storms like this, when he didn't have to walk through them. It was great writing weather.

He pulled a can of chicken soup out of the pantry and heated it in a saucepan on the stove. The old building seemed to creak and shudder with the occasional gales of wind, but Jess enjoyed the pattering of the rain as he buttered toast and poured the steaming soup in a chipped bowl. He carried his dinner to his writing desk, by the large, old window in his living room, and flicked on a few lamps. Then he pulled a cold beer out of the fridge, cracked it open, and settled in his scuffed old chair.

The rain fell in sheets, occasionally slamming against the old window panes, but the storm was softer than usual. He watched the rain fall on the cobblestone street below, illuminated by the wrought iron lampposts. Then he opened his laptop and began scrolling through the chapter that he completed the day before.

The novel was coming to an end. Jess could tell that a conclusion was around the corner, narrative lines beginning to converge and coalesce. He'd forced his characters through the field of major conflict, and was left with the vestiges of shattered relationships and their patchwork reconstruction. Soon, he'd tie off loose ends, find some sort of final catharsis, and set the characters free in one unsteady direction or another. He liked the cycle of bringing them back to where they started, wavering, allowing the reader to develop his or her own opinion on what came next. He didn't feel qualified to say definitively what happened to his characters after he put them through the wringer and left them to their own devices.

But something about this project felt incomplete, unsatisfied. In his moments of writing he had felt as though he had dug his nails deep into the flesh of the novel, ripping it to pieces as he bled chapters for Rory's editing, but he was beginning to worry that he had really only scratched the surface. Something felt superficial, flimsy. He had a nagging sense that he was forgetting something.

It was the best thing he had ever written, but he knew it could be better. There was a distance in the prose, an invisible barrier that lay between the wounds and the reader. If Jess felt guarded and cautious these days, he could see it showing up in his book.

He had taken to reading Gatsby in the last week, relating to something in Nick Carraway's empty, disappointed disillusionment. _There are only the pursued, the pursuing, the busy and the tired,_ Fitzgerald wrote. Most of Jess' life he had felt like the pursuing, driven by a relentless desperation to write himself to pieces. But these days he felt like the tired. He was exhausted by the energy it took to hold himself back and hold himself together.

He sighed and took a swig of his beer. Then he scrolled to the beginning of the chapter and began reading and editing for real this time, ignoring the distance, trying to pull everything to the surface. The rain gusted against the window, and he began to forget himself in the process.

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Matthew, Chris, and Jess had cycled through a fair share of Cedar Bar Reduxes over the years, but their latest version was a small, underground tavern ten minutes from Truncheon Books. It had decent burgers and a couple of pool tables and plenty of solid wood, dimly lit booths, perfect for small group conversations.

The three of them settled in their usual booth, tucked into a back corner. Matthew was already teasing Jess about Rory.

"This is the one, _the one_ , right? The one who you went all googly-eyed for at the open house years ago?"

Jess rolled his eyes. "She's a friend. And she's an editor, you all should get along fine."

Matthew gave him a knowing look, "Only ever a friend?"

"You already know she's a high school ex girlfriend," Jess scanned the drink menu. He was completely unbothered by them harassing him. "But seeing as that it is prehistoric history at this point, I don't think it matters much."

Matthew grinned. "Prehistoric history, huh? So no unresolved tension? Unrequited love? Suppressed emotions?"

"Man, you've been around poets too much," Jess shook his head. "You sound like you're vomiting song lyrics."

Chris agreed. "Seriously, Matthew. We don't all live in _Pride and Prejudice_."

Matthew just shrugged cheerfully. "Just waiting for the day when broody finds someone to fit the jagged edges of that shredded heart."

Jess whacked him with the drink menu. "You're single too, asshat."

"Single and looking for love, not avoiding it like a disease."

" _You're_ a disease."

"You're both going to wind up alone together, bickering and arguing prose versus poetry in some nursing home for ex artist bachelors," Chris signaled the waitress, "time for alcohol."

Jess leaned back in his chair. His friends were dumbasses, but he was grateful for them. Chris was a calming presence, a mediator between Matthew and Jess, the stable and effortlessly relaxed element of their trifecta. He spoke less but when he did, it usually had a bit more gravitas. And Matthew lived with his heart first and his brain second. He was earnest and caring, warm brown eyes openly desperate for someone to share his same yearning for life and love. He and Jess were more similar than Jess cared to admit - while Jess kept his romanticism buried underneath sarcasm, hidden in between the lines of his dark literature, Matthew wore it cheerfully and openly. He wore button ups and sweater vests like the college boy English major he always was at heart, and endlessly badgered Jess on finding love.

Before the waitress came back with their beers, the door opened and Jess saw a familiar head of brunette hair slip into the tavern. Rory scanned the room, recognized him, grinned, and hurried over.

"Hi," she gave the group a small wave, and pointed at the empty seat next to Matthew. "Can I?"

"Of course!" Matthew scooted over, and Rory sat across from Jess. Matthew reached out a hand out to her, "I think we've met, but I'm Matthew."

"Hi," Rory shook his hand. Chris introduced himself as well.

Jess made a halfhearted attempt at introductions. "Boys, Rory's an old friend and an editor. Rory, Chris is a fairly decent human and Matthew's a - "

Matthew interrupted before Jess could finish his rude and foulmouthed introduction. " - an all around total package. So lovely to have you here."

The waitress reappeared with three beers. Jess took a large drink. Rory ordered something and then turned to them, smiling. "So, how's Truncheon Books? Any new developments?"

"It's going alright, we're not on the brink of bankruptcy yet," Chris shrugged. "Although Matthew is arguably trying to get us there with his endless parade of subpar poets."

"One of my 'subpar poets' is the record holder for being our bestselling author," Matthew said dismissively.

" _One_ of your poets," Jess emphasized. "The rest are fighting for holding the record of being our lowest selling author."

"They can't stand that I have our best seller," Matthew confided to Rory, "but you know, let them talk shit. Numbers don't lie."

"Like the number of tanking poetry anthologies you've forced us to publish?" Chris asked lightly.

Rory laughed. "Poetry takes a specific kind of audience, doesn't it? What's your most mainstream work that you sell?"

"Chris has a knack for historical fiction that does pretty well," Jess said, "but we're convinced it's only because people buy them thinking they're smutty historical romance books."

"We pick vaguely provocative cover art to encourage the mistake," Chris said, nodding. "But hey I'm not complaining. Wish we worked on commission, I'd be raking in the cash over these two."

"And Jess has decided he's too good for publishing work and has disappeared for the last nine months," Matthew added. "Seriously, you're lucky if you find him at work, ever. I have no idea why we haven't fired him yet."

"I haven't disappeared," Jess rolled his eyes.

That wasn't entirely true. Jess had been a crappy employee at Truncheon Books for months, often showing up late or disappearing in the middle of his shift because something struck him and he wanted to go upstairs to type it up. But he tried to make it up to them by working irregular hours on nights and weekends, doing inventory at three in the morning sometimes whenever he hit a block in his writing and needed a mindless activity to wipe his brain clean. He had pushed a few of his authors onto Matthew, but took a couple from Chris when Chris' girlfriend's dad died and Chris had needed to take two weeks off to help with selling the house and planning the funeral. Jess was trying, but he knew he needed to step it up now that his novel was reaching its end.

"Jess has been taking time off in favor of writing the next great American novel that he refuses to talk about," Chris explained to Rory.

Rory shot Jess a look, her eyes dancing, "Yeah, I've heard something about that." He narrowed his eyes at her, but he knew he didn't really need to communicate for her to maintain discretion. Rory was smart - she wouldn't announce to the boys that she'd been editing Jess' work for months now.

"We're putting up with it for now, but I swear to god, Jess, if you don't ever finish it, you're paying us a year back in paychecks," Matthew warned.

Jess responded with a rude hand gesture.

The waitress showed up with Rory's drink, and Chris held his glass aloft. "Cheers to everyone idiot enough to work in the literary world."

"Cheers," Rory said, smiling. The four of them clinked their glasses together.

The conversation ran easily, meandering through a few rounds of drinks in the dim corner of the tavern. The group ordered burgers for dinner, and Matthew and Chris laughed uproariously at Rory's stories of high school Jess. Teasing him, she recounted him vandalizing snowmen, showing up with a black eye at her grandmother's uppity house, and participating in small town festivities with all the enthusiasm and grace of an angry adolescent scrooge.

Jess just shook his head, drank his beer, and let them have their fun. He was years removed from his days stuck in that ridiculous town. He was more fond of it now - mostly because it reminded him of Luke - but Stars Hollow often felt like a weird dream to him. The surrealist town holidays and caricatures of townspeople were strange enough, but he couldn't detach the town's oddities from the deep well of emotion he locked up from falling in love there for the first time.

After a while, the conversation, predictably, turned to Matthew's endless quest for love. "I'm refusing to online date," Matthew sighed, "because where is the romance in that? But honestly, I've been ghosted by the last three girls I went on second dates with, so I have no idea what I'm doing wrong."

Chris and Jess laughed, but Rory was concerned. "The last _three_? What are you saying or doing that makes them run off like that?"

Her question only made Jess have to work harder to cough down his laughs. Matthew shrugged, "Oh there's a whole list. I have a bad habit of writing poetry on bar napkins for them. I talk about marriage and kids way too early. I ask inappropriately personal questions about what ended their last relationship."

This time Rory giggled too. "Well . . . yeah, I don't know how to help you then."

"Sometime, someday, I'll meet a girl who isn't scared off by it," Matthew said cheerfully, "but until then, the hilarity parade continues for these two idiots."

She glanced at Chris and Jess. "You all have the privilege of witnessing this?"

"All the time," Jess confirmed.

"Every weekend," Chris agreed. "It's more funny because the girls are always calling Jess back, trying to see him again, and Matthew's drop him after a night."

Matthew made an outraged expression, and began to rebut Chris. Jess just drained his beer at that comment. He wasn't sure he wanted Rory to know how he spent his hours in bars with Matthew and Chris, but he supposed it didn't matter much. Of course she must assume that he wasn't living like a celibate monk, up in his attic writing for hours. But he avoided her eyes all the same.

" . . . Besides, it's not my fault that women _like_ assholes," Matthew continued, "Jess ignores them and they can't get enough of him. I express genuine interest - tell them honestly that I like them - and they can't stand me!"

Rory smiled, her eyes flickering to Jess. "Not all women are like that. You'll find one that likes the honesty and the lack of games."

"Yeah, well, sign me up for one," Matthew groaned, "I can't live this life of heartbreak in dive bars much longer."

The waitress came back, drawn by their empty glasses. They ordered another round and Matthew continued complaining.

Jess looked at Rory, made eye contact, and gave her an apologetic expression that he hoped indicated that he felt bad about Matthew's endless griping. She smiled back at him, eyebrows raised, and for a brief moment, Jess understood Fitzgerald's appreciation for the intimacy of large parties. It was easy, in a crowded and noisy tavern, to meet eyes and communicate with no one watching.

Chris, finally fed up, told Matthew to stop whining and go get quarters so that they could play a game of pool. Rory stood, laughing. "I'll be right back."

As soon as she was gone, without preamble, Matthew and Chris leaned forward, elbows on the table. "Dude, she is _into_ you," Chris said.

Matthew nodded, " _Really_ into you."

Jess drank his beer. "No, she's not."

But Jess wasn't stupid; he could tell that Rory had been looking at him differently. He saw it at Christmas, when she had eyes on him throughout the night, when she leaned into their conversation, playing casually with handfuls of sparks. And he saw it during that terrible storm in New York, when he visited her at the hospital and she carelessly broke down plenty of the carefully constructed, fragile boundaries that had defined their friendship in the last years of running into each other at Luke and Lorelai's. When she had fallen asleep on his shoulder, he had nearly gotten up and left, mostly unwilling to play this game or let her play with his locked up heart. Instead, he had let it happen, but he felt himself being more guarded than ever. _Can't repeat the past? . . . Why of course you can!_ Fitzgerald coaxed him. But he ignored and avoided all of it like a practiced survivor.

"Are you going to do something about it?" Matthew pressed.

"No," Jess said, shortly.

"Why not?" Chris seemed curious. "She seems great."

Jess was getting annoyed. "She brings a lot of baggage."

"Well that's just rude," Matthew was affronted.

Chris tossed a napkin at him. "Not her baggage, dumbass. Their past relationship baggage."

"Ah," Matthew nodded. "So you're not into her?"

"No," Jess repeated.

"Then you're an idiot," Matthew advised.

Their conversation was cut off by Rory returning. Jess was grateful - Matthew and Chris were pointing out all of the signs that Jess had been steadfastly disregarding and evading for months, and he wasn't in the mood to put up with them. He kept that inner part of himself locked up, _tight_.

"Well, we're going to go play a round of pool," Chris glanced at Jess, smirking. "Come join if you want to play doubles."

Jess resisted the urge to hit both of his friends.

Rory sat across from him, her hands playing with her glass. If she was bothered by their conversation about Matthew and Jess hooking up with girls in bars, she didn't show it. Her blue eyes were bright and cheerful, her mouth curved into a slight smile.

Jess, sensing danger, changed the topic. "How's Richard?"

He knew Richard was doing better, knew this was a safe area of discussion.

"He's doing great," Rory said, breaking into a true smile, "really great. Luke told you he woke up?"

Jess nodded. She continued, "He got moved back home last week. He's still on bed rest, and they had to hire an at-home nurse - Grandma's already fired three of them - but he seems like his old self. They let his bridge club come over to play, and he fixed it up in the will that Grandma isn't allowed to sell the house unless she has the actual death certificate in hand."

Jess snorted. "That's cheerful."

"Well, she kept threatening it when he was in a coma, so he's not taking any chances," Rory shrugged. "Mom is over there a few days a week. I visited last weekend but it's been harder now that he's not in the city anymore."

"I'm glad he's doing well," Jess said. He meant it.

"Me too," Rory agreed. She glanced over at the pool tables, where Matthew and Chris were setting up. After a few moments, she spoke again. "Your friends are funny."

"They're something," Jess said matter-of-factly.

"Poor Matthew. I hope he finds someone."

"God knows he's trying," Jess leaned back and took a drink of his beer, "it's exhausting. You're a saint for listening to him for so long. Usually we kick him to the curb and tell him to get over it."

"What wonderful, understanding friends you are," Rory shook her head, amused. "The boy is lonely!"

"Aren't we all," Jess said dispassionately.

Her eyes were glimmering again. She continued looking at him, refusing to play along with his attempts to avoid eye contact. "Doesn't really sound like you're so lonely, Jess."

He felt himself groan internally. He did not want to have this conversation. But he couldn't think of a segue, so instead he stayed quiet, watching the pool tables.

"I'm only teasing," she offered, her tone light.

Jess forced a half smile and deflected. "What about you? Do you have any bad habits of picking up men in bars?" He highly doubted it. Rory Gilmore tended towards the safe and the certain, eschewing spontaneity or bad decision making for thorough vetting and established emotional connections.

"Only one," she said. That surprised him. Then she continued, "I think we're sort of dating now."

That was less surprising. "Good for you," Jess gripped his beer. "What's his name?"

"Noah," she said. Her eyes were on him, curious.

Jess processed quickly and efficiently, ignoring any sort of interior emotion. He kept everything buried. He felt detached and unconcerned, but he could tell that she was looking for his reaction.

"How's the 'sort of' dating going?" he asked. His tone was friendly, mocking.

"Pretty good," Rory said, straightening up slightly, sounding more or less enthusiastic, "He's nice, he likes coffee shops, he can keep up with the Gilmore speed of conversation about half the time."

"Nice, caffeinated, sometimes capable of talking," Jess ticked off his fingers, "I mean really, Rory, sounds like you've found a winner."

She rolled her eyes, smiling, "He's great. And he really likes me, I can tell."

Jess nodded, "Definitely meeting all the bare minimum requirements for a guy you're 'sort of' dating."

If they were sitting next to each other, Jess was sure she would have batted at him. "It's _good_ , really. Going well. I'm happy."

Jess pretended to bow out and take her word for it, but he could sense a hollowness in her _I'm happy_. She was bright and smiling but it all seemed a little too composed, a bit too friendly. It reminded him of something, like déjà vu, but he couldn't quite place it.

"He's sweet and he works hard and he's successful," she added, unable to resist making her argument, like she was laying down a defense. "I'm optimistic."

Jess suddenly realized what she was reminding him of. He could picture it, a seventeen-year-old Rory, steadfastly and stubbornly defending her 'sweet' and 'perfect' first boyfriend even as her eyes followed the lining of Jess' jacket, raking over him while she swore she was ignoring him. She played that game for _months_ , her eyes following Jess everywhere, unable to even pretend to stop her body language from turning towards him, searching for him. She held Dean's arm like a vice grip, threw herself into him, and still watched Jess over his shoulder.

Of course Jess had loved it back then, back when he was risky and shameless and doing everything he could to get her to look at him. But now, he could feel Rory watching him as he listened to her empty words claiming the opposite, and he didn't want much to do with it. He kept pushing away the fear, checking the locks, determinedly refusing to engage. He built up a wall of caution and refused to acknowledge the deep cracks forming in it.

"It sounds like that could turn out great," Jess said. "Happy for you."

She smiled, but it didn't reach her eyes.

"Pool?" He offered, standing up. He was done talking about all of this. He wanted a whiskey and a cigarette and a cold shower and a blackout writing binge.

"Sure," she grinned.

They joined Matthew and Chris, and wiled away the time with a few games of pool. After their conversation, Rory seemed to decide that drinking was the best option for her, and she became rather lighthearted and funny and charming. Jess smiled despite himself as she leaned on her pool stick, her usual rapid fire pace of dialogue only getting worse under the influence of alcohol. She was as magnetic as ever, even in the dim light of the tavern, playing with her dark hair and teasing Matthew when he caught the eye of another doe-eyed undergrad in the corner with a notebook.

At one point Chris sidled up to Jess. "You're sure about her?" He asked in a low voice.

Jess shook his head. "No."

A ghost of a smile appeared on Chris' face, but he stayed calm, pretending to focus on the game. "Seems like she's pretty sure what she wants."

"She's sort of dating someone," Jess said. He said the words automatically, but he knew they didn't really matter. Rory didn't give a shit about this Noah guy.

"Well Matthew's right," Chris said. "You're an idiot if you don't do something about this."

Jess shrugged. "I might be an idiot then."

Chris eyed him. Then he clasped his shoulder, briefly, and moved to take his shot. Jess leaned against the wall. He felt exhausted.

The night concluded after Rory spent a solid thirty minutes coaching Matthew on how to talk to the pretty undergrad in the corner. By then it was late, Jess was irritated and hot and restless and aching for a cigarette, even though he'd been quit for over a year. Rory was clearly a bit tipsy, and Matthew was drunk enough that he was spinning verses out loud, quoting poets and being generally loud and rambunctious and obvious.

They left the tavern. The April night was dark and damp after a week of rain. Rory brushed Jess every so often as they walked, but he couldn't tell - and didn't want to care - whether it was because she was a little inebriated or because she was trying to communicate something.

"What a great night," Matthew exclaimed happily, his voice loud, as they reached the corner where Chris and Matthew would turn towards their apartment. "You guys are the best. Rory, you're the best."

Rory grinned and hugged him, "Wishing you the best of luck in your romantic endeavors. Stop quoting William Blake."

"Yes, ma'am," he saluted her.

"See you all," Chris grabbed Matthew's jacket and gave Jess a look. "Sorry about him."

Rory waved goodbye, and turned up the street. Jess saw Matthew's eyes follow her, until Chris pushed him towards their apartment.

Jess shook his head. He was in a bad mood. He hurried to catch up with Rory.

He didn't want to offer it, but he knew he needed to. "Do you need a couch to crash on? Where are you staying?"

"At a hostel. It's kind of terrible," she shuddered. "A couch would be great. Is that okay?"

"It's fine," Jess said.

He brought her back to Truncheon Books, and then led her up the stairs to his apartment. He flicked on the lamps and grabbed a glass of water and a few blankets. "I'd offer you the bed, but I promise the couch is more comfortable and it's way cleaner in here," he explained, setting up a bed for her on his couch.

She swayed very slightly as she stood, her arms wrapped around herself. She smiled. "This is perfect. I really appreciate it."

"No problem," he tossed a pillow onto the couch and set her water on the coffee table. "Need anything else?"

Rory shook her head no.

"I've got a bit of a headache," he said. It wasn't a lie - his head was pounding and all he wanted was to be alone with a bottle of whiskey and his laptop and a damn cigarette. "Are you cool if I call it a night?"

"Of course," she seemed a little surprised and concerned, "no worries at all, I'm exhausted, I'll be asleep in a minute. Are you okay?"

"Yeah," he forced a smile. "Shout if you need anything."

Before he did or said anything worse, he turned and disappeared into his room. He closed the door and leaned back against it, his eyes closed.

Jess didn't hear anything from Rory. He grabbed a bottle of whiskey from his desk drawer, tossed his laptop on his bed, and began writing, half tangled in his pile of sheets and hitting the whiskey a little too hard and aching for a smoke. But he had no cigarettes - he would not go buy cigarettes - and before long the whiskey smoothed his riled bloodstream and calmed the ache in his head and made his thoughts blurry and muted and less dangerous. But every once in a while he would remember that Rory was asleep on his couch, a few feet away, and he would close his eyes and fervently wish he could just pass out and not deal with any of it.

 _No amount of fire or freshness can challenge what a man will store up in his ghostly heart_ , Fitzgerald advised. Jess swore at him.

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Hours later, the morning dawned, grey and cloudy and threatening April rains once more. The soft light slowly illuminated Jess' mess of a room. He threw down his laptop and yawned. He honestly didn't know if he had slept or not.

He didn't want to be there when Rory woke up. He didn't, or couldn't, deal with seeing her again this morning. His muscles were sore and aching from the effort it took to wrap extra iron bars around everything related to her in that stupid teenage part of his heart. He couldn't deal with her blue eyes or soft voice when he felt this exhausted and tenuous.

Quietly, he gathered his computer and notebooks into his bag, and threw on a fresh t-shirt. He swirled the whiskey taste out of his mouth with mouthwash, and grabbed a jacket.

He opened the door to the living room. Rory lay curled up on the couch, breathing softly, her eyes closed. Strands of her dark hair were strewn across the pillow. She looked peaceful, younger, a vision of her seventeen-year-old self with more prominent cheekbones.

Jess stared at her for a moment, his hand on the doorknob. Then he shook his head and headed for the front door, careful to close it quietly behind him, his heart beating rather loudly in his throat.

Fitzgerald sighed. _And for a moment I thought I loved her. But I am slow-thinking and full of interior rules that act as brakes on my desires._

Jess hurried through the misty morning to a coffee shop, trying to forget.

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* * *

Sending lots of love to everyone who has left reviews! So grateful for wonderful readers.

I promise, things are picking up . . .


	10. Chapter 10: Fourth of July 2011

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 **Chapter 10**

 **Fourth of July, 2011**

Rory hated the New York subway in the heat of the summer. She sat stiffly on the seat, sticky with sweat, already annoyed that she'd have to dry clean her best skirt suit. But the sweltering commute was worth the price, because if Rory was right, she was pretty sure she just nailed her interview with a boutique publisher in SoHo.

She was on her way back to Brooklyn, her knees jittering with adrenaline. The interview had been easy from start to finish. After weeks of prodding - after she almost got the job in Philadelphia, but then found herself out of the running because of a lack of editing samples - Rory had convinced Jess to let her show a chapter of his work marked with her edits, and it had been a resounding success. The interviewer - a high-level, fifty-something editor with cat eye glasses - looked impressed. "You really seem to connect with this text," she observed, flipping through it, "your insights are spot on."

Rory shrugged, "It was easy with this one, he's a great writer."

The editor then tried to wheedle the name of the author from Rory for a few minutes, but Rory laughed and swore up and down that she could only share the chapter on the condition of anonymity, and besides the book was already under contract somewhere else.

"Fine," the editor smiled and pursed her lips, "but if you have friends who write like this, I do hope you introduce them to us sometime."

Rory left in a chorus of handshakes and _so nice to meet you_ and _we'll be in touch_. When she reached the ground floor and exited out to the street, she called her mom, and they screamed together and jumped up and down. It was finally happening, Rory felt. After wasting so much of her twenties with paralyzing unemployment and indecision, she was finally beginning to figure it all out.

She leaned back in the subway seat, resigned to dry cleaning her suit, and sighed happily. She was heading back to Stars Hollow this weekend for Luke and Lorelai's engagement party, she was sure she'd be seeing Jess there, and by the end of the week she might be employed. Everything was lining up.

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Her train on Friday night was late, but Rory didn't care much. Lorelai picked her up from the station, all smiles. "Hey kid," she greeted her, pushing food wrappers off the seat and onto the floor, "train didn't fail of heatstroke?"

"Almost," Rory buckled her seatbelt and closed the door. "It's brutal out there."

"I know it's too hot to eat, but what do you want to eat?" her mom asked cheerfully, "the Indian place is closed for construction, but I think we still have some Thai and Chinese options. And Luke's, of course."

"Luke's," Rory decided immediately. "Extra fries."

Lorelai drove one-handed while she called Luke and placed their order. Rory could hear Luke on the other end of the line, exasperated. "Lor, I _know_ your order. You don't have to . . . Lorelai really, you . . . _Lorelai, I know what you guys want!_ "

" . . . and coffee. Lots of coffee. To go," Lorelai finished, winking at Rory. "Need me to say it again? Did you write it down? I can have Rory text it to you."

"Good god," Luke groaned. "If you say it one more time you're getting nothing. No extra fries, and decaf coffee."

"You wouldn't," Lorelai said, affronted, "I think we're allergic to decaf. I'm pretty sure we'd go into anaphylactic shock. Does decaf come with a complementary hospital visit? We might die."

"See you soon," Luke grumbled.

"Love you," Lorelai chirped, then snapped the phone shut.

"Is he closing the diner for the party tomorrow?" Rory asked.

Lorelai nodded, "For the evening, yeah. Taylor was so mad, especially because Luke explicitly disinvited him from the party, but I told Taylor later that of course he was welcome to join."

"Are you trying to get Luke to call off the wedding on the night of your engagement party?" Rory raised her eyebrows.

"He won't notice," Lorelai said dismissively, "and I'm not going to make Taylor mad when we're trying to get permits to have the wedding in the town square. You'd think I was trying to host a nuclear arms parade, the amount of paperwork we have to go through."

"That bad, huh?" Rory said sympathetically.

"I have to provide character references. _Character references_. I then cheekily asked Taylor to be my character reference and he was not amused. So I had to send him a gift basket to make it up to him and now he's also seeking letters of recommendation and a notarized ethics statement."

"That's awful."

" _And_ we'll get fined if anyone mixes up the separated recycling system or spills anything on the grass," Lorelai rolled her eyes, "I swear, as soon as the wedding is over, I'm going to engage in an ongoing, guerilla campaign of civil disobedience against those damn recycling bins."

Rory grinned. "I'll help. I'm good at mixing up paper and plastic."

"Aw, my brilliant, disobedient progeny," Lorelai gave her a one-armed squeeze. "So lucky to have you."

They continued chatting as they drove down the dark Connecticut highway. After a while they turned down the road to Stars Hollow, and entered the little picturesque town. The lights were on at Luke's but the sign clearly said **CLOSED.**

"I'll be right back," Lorelai said, putting the car in park.

Rory leaned back in her seat and waited, watching, as Lorelai tapped on the door. Luke appeared, scowling, with an enormous paper bag. They chatted for a few minutes, and then Lorelai kissed him and returned to the car.

Rory craned her neck, but didn't see anyone else in the diner. Shaking disappointed thoughts out of her head, she turned to her mom and continued their chatty reunion.

They set up _Eternal Sunshine of the Spotless Mind_ and curled up on the couch, wearing sweatpants and accompanied by half of Luke's entire menu and a couple glasses of white wine. Rory felt content. She munched on her fries and teased her mom about wedding plans and seating charts.

"Well, the guest list has been a journey so far," her mom stretched out her legs, groaning, "I'm trying to prevent half of Hartford society from being invited, and Luke's doing everything he can to keep half of Stars Hollow from being invited. So who knows kid, this may be a _very_ small wedding. Maybe we'll reclassify it as a large elopement."

Rory laughed. "Stars Hollow has to be invited! And just give Grandma a table of ten seats and let her choose who to pick from Hartford society, Hunger Games style."

Lorelai grinned, "Good idea. I already convinced her that her hosting responsibilities will make it so she can't sit at the wedding party table."

"Well done," Rory approved. "Who all is at the wedding party table?"

"You, me, Luke, Jess, Sookie, Jackson, maybe Liz so far," Lorelai ticked off, "Oh, and April of course. I don't think TJ is going to make Luke's cut - " Rory snorted on her wine - "And your date, whoever that is." Lorelai winked at her.

"My date?" Rory repeated. She sipped her wine.

"No pressure, but yes, you are ranked high enough on the guest list that you get a plus one," Lorelai reached for the pancakes, "and whoever it is, we won't make them sit with Emily and the dear Daughters of the American Revolution."

Rory laughed weakly, but took another sip of her wine. It made perfect sense that she should have a wedding date, but she felt undeniably weird having a wedding date at a table that Jess would also be sitting at.

"Does Jess get a plus one?" she asked, trying to play it cool.

Lorelai shrugged. "If he wants one, but I don't think he will." Then her eyes narrowed. "Why the curiosity, child of mine?"

"I just don't want to be the only person at the table bringing a stranger along," Rory protested. The excuse sounded a little pathetic, even to her.

"What happened to Valentine's Day Brooklyn guy?" Lorelai asked, "I thought that was happening?"

"It was," Rory toyed with the stem of her wine glass, "I think I ended it, though."

"You _think_ you ended it?"

Rory shrugged. She felt uncomfortable with this whole topic. She had been having fun with Noah - he was sweet, with his square glasses and calm confidence and love for film and the same types of weird cinema that she and her mom loved. They had a good time together. He brought her to vegetarian restaurants and breweries and she introduced him to all her favorite coffee shops tucked into corners in Brooklyn. She played the role, acted the part, encouraged the script.

But something in her knew it wouldn't last. It couldn't last, not when her head was embarrassingly full of a different type of dark-haired artist. Her cells shuddered differently when Jess was around. She was done pretending to be cool, acting as though she was avoiding the dark waters inside her heart that concealed her unresolved teenage romance. She had toed the edge for months, peering into the deep, nearly pushed in whenever Jess shot her one of his wry half-smiles, or when she traced the sharp lines of his profile with her eyes. In February, when he brought her Thai food at the hospital and accompanied her during one of the worst New York City blizzards in recent memory, she finally threw her hands up, reckless and irrational and unzipped, and dove straight in.

She had used Noah as a life raft, a buoy to keep her head above water. But gradually, as the current got stronger, she found herself slipping away regardless. She liked the distraction of having Noah, but after a while it wasn't enough to keep her from drowning in whatever she felt for Jess.

"I did end it," she clarified. "A few weeks ago."

"A few _weeks_ ago?" Lorelai repeated Rory again, outraged. "What, you just don't tell me things anymore?"

"I was going to tell you," Rory leaned back, sighing. "It didn't feel like a big deal."

"But your wedding date feels like a bigger deal?" Lorelai asked shrewdly.

Rory took a very large, deliberate bite of cheeseburger, and chewed on her response. She swallowed. " _No_. I was just asking, for logistical reasons, because if my hypothetical wedding date is the only stranger at that table, I'll feel weird. Should I just bring Lane as my date?"

"No, you should not 'just bring Lane as your date,'" her mom said, scandalized. "Besides, Lane is already invited. And last I checked, she has three dates, all immature boys."

"Paris?" Rory suggested.

" _Rory_ ," Lorelai countered, raising her eyebrows.

Rory stared at the television. She drained her wine and poured herself another glass. She wasn't ready, really, to have this conversation with her mother, but then again they did talk about everything and Rory was resigned to the Jess-related floodwaters that she was treading water in, patient, wanting. She was sure her mom would figure it out anyways the next day, when Jess showed up at the engagement party and Rory undoubtedly acted like a transparent idiot.

"Does this have anything to do with you editing Jess' novel?" Lorelai asked. Her tone was softer, coaxing.

"Maybe," Rory said, stiffly.

Lorelai hesitated a minute. Then she poured herself another glass too. "Look, Rory, I'm not stupid. It's totally fine if you're all into Jess now."

"I'm not _all into Jess now_ ," Rory countered, combative. But then she relented. "I am, maybe, a little bit into Jess now."

It was very odd to say it out loud. Rory focused her attention on her glass of wine, the blood rushing to her cheeks. As unzipped and illogical as it all was, Rory felt some settling sense of honesty in telling her mother the truth of the tempest.

Lorelai cracked a large, insuppressible smile. But she pretended to be casual, watching the movie, popping French fries. "I was wondering if this would happen. _Editing his book_. If that isn't a cover for an illicit romance, I don't know what is."

"I did edit his book!" Rory protested. "It's been a _year_ of it. He sends me chapters in the mail, I mark them up and mail them back to him."

 _Mark them up and mail them back to him_ was the most nonchalant way Rory could have possibly phrased _consumed the chapters like a raving addict, poured heart and soul into editing comments, flung chapters back in the mail as fast as possible to get another fix soon_.

"And it was just editing? No cute romantic notes attached, no phone calls late into the night about sexy things like grammar and syntax and punctuation and years of romantic history?"

"Nope, just editing," Rory said firmly.

"Well that's so much more boring than it could have been," Lorelai reached for her wine glass. "I was hoping for some juicy story of you two holed up in a bar or library somewhere, editing into the dark of the night, drunk on words, meeting of the minds turning into some wild, late night - "

" _Mom_ ," Rory said, sternly. She sipped her wine and sighed, "Besides, I'm getting the feeling that this is a one-sided thing."

"A one-sided thing?" Lorelai repeated incredulously, "you think he's not 'maybe a little bit into you?'"

Rory shrugged, her eyes on the television. There was a sinking feeling somewhere in her abdomen, a sense of fragile disappointment that acted as a constant chill on her interior emotions. So far, Jess had shown nothing resembling a reciprocity of emotion. He was funny and sarcastic, open to spending time with her, perfectly relaxed in whatever friendship they had struck through editing. But he maintained a consistent, careful, unrelenting distance. Rory could feel it physically, in the way he ever so slightly angled his body away from hers, or created an extra inch or two of space between them when they walked. She could also tell that he was refraining from talking too much about their personal lives, about whatever romantic mess either of them found themselves in. He painted a picture of friendly curiosity about Noah, but seemed unbothered and uninterested. When his friends mentioned Jess taking girls home from bars, Jess had rolled his eyes and rejected the line of conversation, steering them carefully to less personal territory. As much as she didn't want to admit it, Rory could tell that Jess had built a series of invisible barriers, a protective shield, and he had no intention of removing them.

"He hooks up with girls from bars sometimes," Rory said idly.

"Of course he does," Lorelai was unperturbed. "Any girl going into a bar by herself is looking for something that looks like Jess. Jess looks like trouble in the good way."

Rory was vaguely annoyed by this. "Trouble in the good way?"

"Yeah he's the John Bender, the Jim Stark in _Rebel Without a Cause_. Nobody aiming for a hook up goes to a bar looking for a sweet Prince William to take them home - they go looking for a young Johnny Depp smoking a cigarette in a dark corner."

Unbidden, a memory arose of seventeen-year-old Jess, looking very much like Jim Stark, leaning against a gas station, toying with a cigarette, waiting for her.

"I know," Rory sighed.

"Kid, Jess has been hopeless for you for years," Lorelai said, firmly. "Ever since he got shipped off to this town, years ago. And if he seems like he's not interested, it's because he's good at putting on an act and you probably scare him because you're different than any of those girls he's finding in bars in Philadelphia."

"So then what?" Rory asked. She was deflated, frustrated.

"Wait him out, play the long game," Lorelai smiled. "Sometimes the long game is worth the wait."

Her mother's engagement ring glinted in the light of the TV. Rory emptied the wine bottle into her glass.

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The next morning, Rory grabbed her copy of Shakespeare's _A Midsummer Night's Dream_ and curled up on the front porch bench with a steaming cup of coffee. She wanted the madness and the comedy, wrapped in fairy magic in warm summer nights. If she was going to feel unzipped and illogical and frustrated by romance, she may as well do it with Puck and Titania.

Shakespeare was a prophet. _And yet, to say the truth, reason and love keep little company together these days_. Rory sipped her coffee.

The engagement party started in the late afternoon, when the smell of barbeque began to drift in the summer heat. The party should have happened months ago, closer to the actual proposal, but it was delayed by Richard's time in the hospital and long road to recovery. Lorelai acted cheerful and blasé about it, but to Rory her mother's voice sounded just a little hollow. All three of the Gilmore women were worried about Richard.

"Grandma, Grandpa!" Rory hurried to the van that was idling on the edge of the town square. "And, uh, hi, I don't think we met," she reached out her hand to the harried looking nurse that was trying to open the back doors.

"This is Simone, she's the new nurse," Emily threw Simone a look of deep skepticism.

Simone glanced at Emily with fright, and then hastened to unload Richard's wheelchair from the back of the van. Richard himself was sitting up front, jovial. "Rory, it's good to see you!"

"Good to see you too, Grandpa," Rory opened the door and gave him a hug. "You look great!"

 _Great_ was a term of shifting meaning these days. Compared to this time last year, Richard looked pale and drawn, his skin like paper, his hair thinning. He had lost a large amount of weight, and sagged slightly in his chair to the left. But he was still dressed impeccably, and his voice was no less booming.

Simone helped him out of the van and into the wheelchair. "It's just easier for me to get around this way," Richard explained, looking around the town square with interest. "Now where's Lorelai?"

Rory smiled. She was used to the wheelchair at this point, and grabbed the handlebars to begin moving it. "I think Mom was helping set up the food. This way."

They left Emily to berate Simone about the proper way to park the van, and meandered through the town square to the corner by Luke's, which was set up with tables of corn on the cob and potato salad and watermelon and barbeque. Luke was standing there, arguing with Sookie.

"The burgers are fine, Sookie, they don't need a jalapeño jam."

"Just a little?" Sookie wheedled, proffering a jar. "Or here, what about a nice garlic and pepper aioli?"

" _No_ ," said Luke. "Put it on your own damn burger, but this is a free country and a condiment optional table."

"But people will make the wrong choices," Sookie insisted. "Look, I brought homemade pickles too!"

"Set it all next to the ketchup and mustard," Luke pointed. When Sookie seemed to hesitate, he repeated himself, warning. "Sookie, with the condiments!"

Sookie grumbled and set her cache of gourmet burger ingredients on the checkered tablecloth next to the relish. Luke, exasperated, turned to Rory and her grandfather. "Rory, hi. Richard, good to see you, you're looking great."

"So I keep hearing," Richard smiled, "these burgers look marvelous, Luke, could you - "

" _No_ ," Emily snapped, appearing suddenly on Rory's other side. "Richard, you know the doctor's orders. Lorelai said that some Korean woman is making you a vegetarian burger."

Richard sighed as Emily pushed his chair over towards a picnic table.

The engagement party mingled with the town square festivities. As the afternoon turned to evening Rory shared three different helpings of dinner with her mom, and smiled as Babette and Miss Patty cooed over Lorelai's ring.

"Where has he been hiding the cash for this thing?" Miss Patty demanded, glancing at the diner as if expecting to see rolls of bills hidden in the siding. "Darling, this is magnificent."

Babette nodded fervently in agreement. "What a flasher. Sugar you better hide this or Taylor is going to start taxing it."

Lorelai laughed, "Well, I guess this is the pay off when you don't get engaged for _decades_."

Rory snorted into her punch, and tried to recover. "Miss Patty, which of yours was your favorite engagement ring?"

Miss Patty launched into an impassioned recollection of Eduardo, some Argentinean dancer that she met "while touring the continent." Lorelai and Rory exchanged a look and had to fight very hard to suppress their giggles.

As the shade stretched over the town square, and the moths began fluttering over the candles on the tables, Rory saw a familiar old car sputter around the corner and park next to Luke's. She felt the color rise in her cheeks, and refocused intently on the conversation before her. But out of the corner of her eye she saw Jess, in a black t-shirt and jeans like a vintage poster from _The Outsiders_ , twirl his keys around his finger and slide into the diner.

Before she could make up an excuse to go inside, her grandmother appeared at her shoulder. "Your grandfather is going to be the death of me," she snapped.

"What, why?" Rory glanced at her grandpa, who was talking happily with Lorelai.

"He's now gotten three different townspeople to fetch him one of those nasty burgers. I only barely managed to confiscate the last one. What part of doctor's orders does he not understand?"

Rory sympathized with her grandpa. "Well, it is the Fourth of July. I know he's tired of being vegetarian."

"But he's _ill_ , can't he understand that?" Emily was irritated.

He was ill. Rory and her grandmother looked at Richard, who, despite his smile and animated hand gestures, was looking older and weaker by the day. In his chair he looked so much smaller, a hunched version of his usual tall and gregarious self. He looked pale in the dimming evening light.

"Is he getting any better?" Rory asked softly, after a few moments of quiet.

Emily maintained her prim posture, but her eyebrows pinched slightly. "No, not really," She said stiffly.

The quiet stretched a little longer this time. Rory crossed her arms, shielding herself from that terrifying sadness that sometimes seemed to well up whenever the Gilmore women talked about Richard. She shook the thoughts away. "He looks good today," she said, trying to be positive, "and who knows, maybe he'll turn around soon."

Emily snapped out of it as well. "Well I should hope so," she said, busily, "because we have a gala at Yale next month and I look _ridiculous_ standing next to that chair in photographs."

She touched Rory lightly on the back and returned to Richard and Lorelai, fussing over the collar on Richard's shirt.

Rory watched her grandparents for a moment, feeling an aching tenderness in the warm summer evening. But before she could turn around, she felt a nudge against her shoulder blade.

Jess' eyes were on her grandparents. He handed her a cold beer. "Wheelchair, huh?"

"Taylor will give you a ticket if he sees you drinking out here," Rory warned him. She took the beer anyways. "And yeah. He doesn't need it, but he needs it."

He nodded with understanding, and continued with the lighter thread of her response. "Half the people out here are drinking, you think I give a damn what Taylor thinks?"

Rory giggled. "You know Taylor will leap at the opportunity to give _you_ a ticket."

Jess made a face of agreement. "Well then let's go find a place to sit where he can't see these then, how about that?"

They meandered to the diner steps, and sat next to each other, keeping the bottles on the step below, behind their legs. Rory felt her cells buzzing. She tried to be casual, tried to look out over the festivities, but she was acutely aware of his tan forearms and his messy dark hair and the way he smelled like whiskey and pine trees. She was hopeless, but she didn't mind it.

"How's the party been so far? I got stuck in traffic."

"Fine, the usual," Rory replied. "There's a George Washington impersonator walking around somewhere, and I thought I saw an enthusiastic Lincoln but it also could have just been a guy in a top hat. Someone put Kirk in charge of the fireworks so I think Luke has four counties worth of fire departments on standby."

Jess shook his head. "This place is something else."

"It's pretty great," Rory said, cheerfully agreeing.

"That's not what I meant," he said flatly.

"I know," she smiled.

They each took a drink of their beer. Although he seemed calm, there was something tense about Jess' posture, about the way he set his beer down a little too hard. His knees were angled slightly away from hers, and he looked rather intently out over the square. Rory was used to his unflinching eye contact, the searching way he would look at her and the pointed questions that would follow. But now he seemed unwilling to meet her gaze.

"Everything alright?" she asked lightly.

"Yeah, of course," he glanced at her, barely, and then looked back at the square. "Sorry, I've had a lot on my mind lately."

"How's the book going?" She asked, understanding.

There had been a few, long months where she hadn't received anything in the mail from Jess. She knew the book was nearly wrapped up, and back in April she had read a chapter that hinted at a conclusion, but she hadn't seen a true ending yet. When she texted and asked about it, sometime in late May, he responded with a short _stalled._ She didn't ask again, not wanting to pressure him, but the lack of manila envelopes often made her feel down and empty, unsatisfied, impatient. Her addiction to his writing was a monster, but she'd done her best to keep it under control while he dealt with whatever was blocking his progress.

"Like shit," he said, honestly.

She waited. The summer breeze ruffled her hair.

"I don't know," he sighed, and took another swig of his beer. "I just feel like there's something missing. It's distant."

Rory toyed with the word _distant_. "There's a lot in there that is emotional and beautiful, right at the surface," she said slowly, "but I think sometimes it feels like _someone's_ emotions and not _yours_."

"It shouldn't be mine," Jess said, with a hint of surprise. "I'm writing characters, I'm not writing myself."

"Well, yeah, but your characters are mouthpieces." Rory struggled to come up with the right words. "It's like . . . sure the characters are fictional and the problems are fictional, but the emotions need to be real. And sometimes it feels like . . . like maybe you're writing about emotions but not with them?"

A great shout of applause came from the gazebo, and Rory could see that the band was wrapping up in preparation for the next group, which would play during the fireworks. Jess was staring straight ahead, his eyes narrowed, thinking.

"I mean, Jess, I think it's _brilliant_ as it is," she backtracked. "If I had felt an emotional disconnect I would have told you ages ago. It's so good, and raw, and real. I'm only saying what I'm saying because you feel a distance, not because I as a reader feel a distance."

"You don't?" he asked, skeptical.

She tipped her shoulders. "Not really. I can see what you're saying, because I know you, but no, I don't think the typical reader would notice."

"But wouldn't it be better if it was actually raw and real?" he said, frustrated.

"Yeah, probably," she said honestly. "But it's already great."

"I want it to be better," Jess said. "It isn't getting published until it's there."

She looked at him, her eyes skimming his profile and the sharp of his jaw line, and felt her abdomen twist. She ignored herself. "Anything I can do?"

"No," he said. His tone was a little short.

Rory raised her eyebrows and took another sip of her beer. She wasn't offended - she knew Jess well enough to know he wasn't trying to be rude - but she was a little worried about him.

After a few minutes of silence, she decided to change the subject. "I had a good interview earlier this week at a publishing house in the city."

"Really?" he raised his beer, tapping it against hers, "Congrats, big Yale editor! 'Bout time."

"She loved your chapter," Rory smiled, "tried to get your name from me for a while, but don't worry, I protected your privacy. They couldn't even torture it out of me."

Jess snorted. "I'm under contract, there's not a damn thing I can do about it."

"Well, I think that sealed the deal," she said. "I was dead in the water before you let me share that around. I really appreciate it."

He shrugged. "You're a good editor. They should see that."

"Thanks," she said.

"How's everything else?" Jess asked. He seemed like he was more relaxed. "Brooklyn? Tutoring? The guy you swear you picked up in a bar?"

"I _did_ pick him up in a bar!" Rory said, offended. But she felt a twist of something like self-satisfied pleasure that Jess had remembered that conversation and still had it on his mind. She continued. "Everything in Brooklyn is good. Tutoring is fun, I had a few high school students get great SAT scores back. And I broke up with Noah."

Jess didn't react at all, aside from taking another drink of his beer. But he seemed a little amused. "Why?"

Rory just made a face. She wasn't about to tell Jess the real reason, because she wasn't one to take a gamble with zero chance of a payout.

"Well I can't say you sounded too thrilled about him back in April," Jess stood and stretched, collecting their two empty bottles. "I'll get us a refill."

He disappeared back into the diner before Rory could rebut him. She bit back a smile. Jess wasn't wrong, of course, but she had _tried_ to put on a good act back in Philadelphia, hanging out at the bar with Jess, Matthew, and Chris. And Jess had just seemed unconcerned, amused in that infuriating way of his. He dismissed Noah easily.

She buried her head in her hands, willing herself to think about something, _anything_ else, but her heart was not cooperating and her pulse beat more quickly. _Lord, what fools these mortals be!_

Jess tapped the cold bottle against her bare arm and she jumped, gasping. "Sorry," he chuckled, and handed it to her properly.

She threw him a look, and took a drink.

"I'm assuming," Jess continued, as though they had been having an actual conversation about Noah, "that you ditched him because he was boring and because you found him at a bar. Men that you find at bars are always boring."

"Aren't you a guy at a bar?" Rory shot back.

"Sometimes," Jess said, carelessly.

"You're not boring," she pointed out. A second later, she regretted it, because she realized it sounded like a comparison to Noah.

"I'm sure plenty of people would beg to disagree," Jess replied, without skipping a beat. "Am I right, is that why you dumped him?"

"No," she said. "It wasn't because I found him at a bar. And he's not boring! I just . . . I don't know, I wasn't feeling it anymore. I have high standards."

Jess laughed, trying to suppress it by coughing into the crook of his arm. "You do not have high standards!"

Rory gave him a withering stare. He continued laughing. "You dated _me_ for chrissake. And god, Dean. And whatever that blonde dick's name was. Rory, you haven't had a decent boyfriend yet."

Even as he insulted her past romantic history, Rory felt herself fighting a smile. She liked the pathway of this conversation, and she felt a little internal burst of sparks at the brief acknowledgement of their shared romantic history. She found herself grinning, knees turned towards him, eyebrows raised in challenge. "Okay, first of all, Dean was great. Perfect first boyfriend - "

"Perfectly _boring_ ," Jess interjected.

" - and Logan was only bad sometimes, for the most part he was sweet and amazing - "

"A sweet, amazing asshole," Jess countered.

" - and _you_ were wonderful, even if you needed some help to figure out how to be a decent boyfriend," Rory finished.

"Thanks for giving me the only caveat," Jess' eyes glinted. He was animated now, turned towards her, his half-smile in full effect.

"Well," she shrugged, feeling fun and dangerous, "you did have a bad habit of not calling. And disappearing. And generally doing everything you could to dismantle us." She took a sip of her beer. "But I've never been able to talk to anyone like I was able to talk to you."

She kept the past tense on purpose. The sun was nearly down now, the moths flitting around the porch light of the diner above them. Jess was smiling.

"Later girlfriends would thank you for the - what did you call it - _help_ you gave me on figuring out how to be decent."

"You needed a lot of it," she teased.

"And you need to have higher expectations for men you pick up in bars," he stretched his legs out.

"I'm fine with the expectations I have for the men I'm trying to pick up," Rory contradicted, her tone light. She chose the present tense for that one.

Jess could have commented on it, could have immediately called her out on her transparency, on the way she _knew_ she was probably looking at him, underneath her lashes. But he kept everything on the surface, even as he let himself relax, even as the conversation pulled into a direction that he usually avoided.

"I'm just saying Rory, aim higher," he advised. He gently knocked one of his knees against hers. "And don't let yourself be bored by men from bars."

She felt electric, in the heat of the evening. The crowds in the town square in front of them were setting up camping chairs, laying out blankets, arranging themselves for the fireworks that were sure to burn down at least one historic building. She saw Luke yelling at Taylor about something, gesticulating angrily. Everything felt like it was buzzing. Her knee tingled from where he'd touched it.

"I'll try," she rolled her eyes. "I promise you this much, I'm not looking to be bored."

"Good," he flashed her a smile. "Life's too short for that."

"Isn't it ever," Rory agreed. She was facing him, watching him, refusing to shy away from the topic.

It was the eye contact that did it. Her blue eyes met dark brown, and suddenly, instead of being loose and relaxed, teasing and (though she hardly dared to think it) flirtatious, Jess seemed to freeze. He looked away quickly. Something shifted, his energy disappearing behind the familiar, cautious wall that he usually kept between them.

He stood, a little too rapidly. But, with his usual ability to act natural and unaffected, he gave her shoulder a small squeeze. "I'll be back in a bit." And he disappeared inside the diner.

When the door slammed shut, Rory sighed and placed her chin in her hands.

She was spinning. It was so easy, too easy, to get caught up in Jess and the banter they shared. She already knew she was lost. She was resigned to it.

But maybe - she raised her head and glanced back at the diner, at the closed door. Maybe Jess was losing himself too, and he just wasn't willing to face it.

Rory knew she was thinking like a hopeless cause, like a mortal in Shakespeare's woods blinded by a fairy love potion, but she had an instinct and an intuition that was usually, always right. Maybe her mother was on to something, maybe Jess was just good at putting on an act.

She played with her hands, watching the crowd, lost in her thoughts. The air still smelled like Jess' cologne, like whiskey and pine trees.

Perhaps her mother was a prophet, and this was the long game. Rory didn't know how long it would take to deconstruct Jess' wall, brick by brick, conversation by conversation, but she was fairly certain she could do it. It almost seemed as though he was afraid of her, afraid of what she could do.

Feeling lighter, with something of determination or recklessness or joy bubbling in the usual dark waters that housed her feelings for Jess, she stood and went to join her mom for fireworks.

It could be a dream, or an illusion, but Rory was content to stay under the influence of love-in-idleness until Jess saw fit to join her.

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Wow, thank you for all the substantial, long reviews! Your feedback is such an inspiration to keep writing.


	11. Chapter 11: Halloween 2011

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 **Chapter 11**

 **Halloween, 2011**

 _Everything was beautiful and nothing hurt_. - Kurt Vonnegut

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Jess got the call from Luke early in the morning. The sun was shining weakly through the fall foliage into his kitchen while he waited on the pot of coffee to finish brewing. He was exhausted, resting his forehead against one of the kitchen cabinets, eyes closed.

"Hello," he answered the phone, his voice still gravelly from sleep.

"Hey Jess," Luke said, weary.

"Did it happen?"

Luke sighed heavily. "Yeah. An hour or so ago. Lorelai's a wreck."

Jess waited. The coffee pot sputtered, steaming up the frosty window.

"The funeral is going to be in a few days," Luke told him. "Lorelai said you should come, if you want to."

"Should I come?" Jess asked, curious.

Luke seemed tired. "It'd be nice for me to have you around. And I'm sure Rory would appreciate it."

"Okay," Jess said. "Hartford?"

"Hartford," Luke confirmed. "Monday afternoon."

Jess hung up the phone, and poured himself a cup of coffee. He glanced at the calendar tacked to the wall. Monday was the 31st of October. Halloween.

Jess took his coffee to his desk and sat heavily in his chair. Chilly, morning autumn air seeped through the cracks in the window pane, and Jess pulled his sweatshirt sleeves over his hands. He held his coffee and looked out at the damp fall foliage. The fog was burning away as the shallow sunlight filtered to the cobblestone streets, but it was a melancholy morning all the same. His pounding headache probably didn't help.

He pushed _Slaughterhouse-Five_ off of his laptop and flipped it open, wincing at the brightness of the screen. Despite brushing his teeth twice and drinking coffee, his mouth still tasted like whiskey.

Fighting with an ongoing writer's block, Jess had fallen into familiar bad habits. He drank himself into a whiskey stupor most nights, staring at the blinking cursor on a blank word document, aggravated and fatigued. It wasn't just his book that was blocked - his nearly completed, close to perfect, _almost there_ book - Jess himself felt like he was detached from the world, from time, from everything. It was like his brain had cut off all connection to his heart, rewired and detoured itself to avoid any sense of emotion. Jess couldn't see into himself, couldn't feel anything.

Vonnegut, in all his wisdom, hinted at the cause of the disconnect. _How nice - to feel nothing, and still get full credit for being alive._

Sometimes, late at night, many inches into a bottle of whiskey, Jess would lean back in his chair and close his eyes and avoid Vonnegut's pointed references to Jess' self-imposed anesthesia. Because somewhere in his subconscious, in the parts of his mind that murmured disobediently under the influence of alcohol, he knew that he was forcing himself into an impossible corner. He wanted desperately to pour the necessary emotion into his book to finish it, but he flat out refused to acknowledge feeling anything in his own heart.

So, his brain rewired itself while his heart beat silently, neglected and ignored and isolated, and his book remained stuck in limbo. And the whiskey was never enough.

Jess checked his watch. 8:00 am. He'd have to be downstairs to open the publishing house in half an hour, and then he'd need to tell Chris and Matthew that he'd be out of town again for a day or so.

He picked up his phone and opened his messages with Rory. They had been talking more regularly lately, a steady stream of book and music recommendations and teasing comments and something that tasted like flirting that made Jess hot and uncomfortable and itch for a cigarette. Everything with Rory made Jess feel like he was on edge. He enjoyed their conversations, and would usually find himself swept up in the moment, bantering and bickering, saying things that hinged on risqué, unable to prevent himself from matching her provocative wit and her lingering suggestions. But then he'd find his head, swear at himself, and pull everything back.

Nothing good was going to come out of fucking with his friendship with Rory. Jess was unwilling to think about old wounds and love lost, a stupid episode of his teenage years that sent him reeling into his twenties. Those locks were there for a reason.

Their most recent messages were a few days old. He hadn't heard from her in a while, not since she called him on her way to Hartford, panicked, driving to the hospital. The call only lasted a few minutes, and Jess could hardly get a word in through her Lorelai-esque barrage of worry and rambling, but he understood the basics. Richard was back in the hospital, and it was serious, and Rory was risking her job to try to get to Hartford in time.

The silence in the last few days had felt heavy and strained. Jess got updates every once in a while from Luke, but he had refrained from reaching out.

Now that it was all over, everything felt different. He tried to type a few different condolences, once, twice. But the words seemed inadequate and pathetic.

 _Sorry_ , he finally typed, and hit send.

He threw his phone on the desk, drained his coffee with a couple of aspirin, and stood to get ready for work. His headache throbbed, and he felt a pull of sadness for the man who had departed the world that morning.

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Sometime during the service, in a high-ceilinged, capacious, echoing church in Hartford, Jess realized absently that he'd never attended a funeral. With all of the loss in his life, it felt odd to him that he'd never attended a formal service.

He sat next to Luke, in a pew a few rows back from Rory and her mom. The church was full of Hartford society dressed in their finest. Jess felt a bit off in a suit, but it was right to be wearing one for Richard's funeral. The service was stately and elegant, much like the man who was now gone.

Of the Gilmore women, Rory was the one to stand and speak. Jess watched, intently, as she stood before the crowd and began telling them about her grandfather. She was sweet and funny, weaving stories in that lighthearted and deeply observant way that Rory always had about her. And though he could tell that her hands were shaking, and a few tears slid down her cheeks, her voice was steady and she smiled as she honored the man who had always been her rock, the sole patriarch of a family of strong-minded women, the keeper of the peace and the voice of reason. Jess, though he tried to ignore it, was impressed, and felt something like pride or admiration or something much more tender tug at his disconnected and cauterized heartstrings.

She returned to her seat, and leaned her head against Lorelai's shoulder. Jess realized he was staring, and looked down at his clenched hands.

The reception was at the Gilmore house. Jess spent most of it in a corner, trying to stay out of the way. People were so crowded around the three women that Jess only saw Rory and Lorelai a few times, besieged as they were by well-meaning well wishers. He often found himself shoulder-to-shoulder with Luke, who didn't want to speak to anyone but clearly felt like it was his sole duty to make sure Lorelai never ran out of coffee or snacks. As the evening grew later, Luke switched Lorelai's coffee for gin martinis.

Jess volunteered twice to go to the store, to get more ice, and stayed in his car for a while in the parking lot of the supermarket, head leaning back, eyes closed, swearing at himself that he would not buy a pack of cigarettes. Inside, the supermarket was full of harried looking parents trying to buy last minute Halloween candy, tugging along small, excitable kids in costumes. Jess clenched his fists as he paid, and managed to get back to his car without smokes. But when he got back to the Gilmore house he took the entire bottle of whiskey off the bar cart and slipped into the kitchen for a while, downing a couple shots, relishing the burn.

 _People aren't supposed to look back_. Vonnegut had written. _I'm certainly not going to do it anymore._

After a few minutes, Rory followed him in through the side door to the kitchen. Her slim black dress made her pale, delicate features and her vivid blue eyes seem more shocking than usual.

She grimaced at him. "Hiding?"

"Medicating," he held out the bottle to her. "Need some?"

Rory took it, without hesitation, and downed a gulp. She wrinkled her nose and shuddered. "Oh, god."

He took the bottle back, amused, and set it on the counter.

"Thanks for coming," she said, crossing her arms. "You didn't have to."

"Luke told me I should," he replied.

She just looked at him, her bright eyes sad and piercing. He felt hot, and self-conscious, but after a moment she glanced down at her hands. "It's nice to have you here."

Jess felt an odd twist, internally, a need to wrap his arms around her. The whiskey told him to fuck it, but he stayed with his back against the counter, tense.

"Are you doing okay?" He asked.

Rory looked back up at him, shrugging. "Yeah I'm okay. Trying to be there for Mom and Grandma."

He knew what that meant. "Have you been doing most of the work, putting all this together?"

She gave him a sad smile. "Someone had to."

Before he could respond, before he could offer to help, to do anything, a voice from the other room called for Rory. She raised her eyebrows at him. "Save me some whiskey for later?"

Jess smiled weakly at her and nodded. She disappeared, back into the reception, and he groaned. He downed another shot of whiskey.

He wasn't surprised that Rory was handling most everything. Every time he had seen Lorelai in a crisis, she was scattered, chatty, quick to make snap decisions and equally quick to change her mind. She meant well, and cared too deeply, and couldn't, or didn't, have the capacity to deal with things like flowers or mourners or hymns or caterers. Rory was always too old for her age, too responsible, too used to taking care of her little family of two.

But he knew that Rory was good at putting on a show, good at holding all the pieces together while people were watching and her mother needed her. It didn't mean Rory wasn't also a mess - it just meant Rory put her family first and buried her own grief deep.

Jess toyed with his shot glass, feeling the whiskey in his bloodstream. Then he placed it in the sink and slipped back into the reception, to find Luke. He probably couldn't do much for Rory while she was kept busy by finding napkins and shaking hands and taking care of her mother and grandmother, but he could be there with whiskey and sympathy later, when the night got dark and empty and quiet.

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By the end of the night he could tell that Rory was beginning to falter, that her carefully composed exterior was starting to break from grief and exhaustion. Like her mother, she switched to gin martinis, and by the time the last people left he could tell that she was feeling the effects in the careful, deliberate way that she closed the front door and stayed balanced in her high heels. Her hair, which was up in a sleek knot for most of the day, was beginning to fall down, dark tendrils brushing her bare shoulders.

Luke clapped Jess on the shoulder. "Thanks for being here and helping out."

"No problem," Jess said. "How's Lorelai?"

Luke glanced over Jess' shoulder, to the living room, where Lorelai presumably was. "I think she's okay. Needs to go to bed soon."

Jess nodded. "Probably a good idea. It's been a long week."

"It's been a long year," Luke sighed. "You heading back to Philly tonight?"

"Haven't decided yet," Jess said. "Gonna check in with Rory, see if she needs anything."

Luke gave him a short, appraising look, but didn't say whatever Jess was sure he was thinking. Instead he patted Jess on the shoulder once more, and walked off towards the living room.

Jess found Rory clearing up plates in the kitchen, her eyes distracted, eyebrows furrowed slightly with sadness.

"Hey," he leaned against the doorframe. "You busy?"

She made a sort of helpless expression, gesturing around at the messy kitchen. "Grandma fired the maid right before she went to bed."

"Right," Jess glanced around at the dishes, careless. "But are you busy?"

Rory looked confused, but she shook her head no. She wiped her hands on a dish towel.

"Want to get out of here?" He offered.

She seemed hesitant. Jess rolled his eyes. "Rory, your grandmother went to bed ages ago with a massive dose of sleeping medication and a bottle of gin, and Luke's taking care of your mom. Do you want to get out of here? I can offer whiskey and sympathy."

She broke a tentative half smile, and nodded. "Whiskey at least, you're terrible at sympathy."

"Not today," he assured her, and guided her out of the kitchen.

He drove to downtown Hartford, looking for any sort of college bar or Irish pub that wouldn't put them in danger of bodily harm. Rory sat in the passenger seat, her arms crossed, her eyes unfocused. Usually his car smelled like stale cigarette smoke, from years ago, but she made the small space smell like rosewater and coffee.

Eventually, he parallel parked in front of a bar near Trinity. It didn't look like much, but it looked functional enough.

Before they got out of the car he shrugged off his suit jacket and tie, tossing both in the backseat. Rory gave him a quizzical look. "Are we too fancy for a bar right now?"

She was in a dress and heels, and he was still wearing suit pants and a collared shirt, but he shook his head no. "We'll just make everyone else look bad," he promised.

When they walked in the pub, Jess remembered - for what felt like the tenth time - that it was Halloween. There were cobwebs strung up around the bar, and dangling cardboard spiders and ghosts. The bar was full of groups of laughing people, most of them in costume. It felt like a night of lighthearted revelry, of manufactured spookiness and obligatory partying. "Monster Mash" played from an old jukebox in the far corner.

Rory raised an eyebrow at the Halloween partying. "Oh. Right."

"Sorry," he frowned.

"No it's fine," she reached for his shirt sleeve and tugged him towards the bar, "looks like the place has whiskey, it works."

Amused, he glanced at her hand on his sleeve and let her lead him towards the bar. Jess ordered them two short glasses with double shots of a dark, amber liquid, gave the bartender his credit card to start a tab, and then joined Rory against a wall in the back corner of the bar, removed from the uproarious crowds around the pool tables and dart boards. He stepped over the lost and discarded pieces of costumes on the floor, and rolled his eyes. Jess was always game to spend a night drinking too much in a bar, but he never acted like a public idiot. He tended to just get moodier, more internalized, more likely to make eyes at some woman and let her diffuse his simmering tension. The frat atmosphere of Halloween in a college bar made him feel old and irritated.

They found a space below a glowing neon beer sign, with a small ledge at shoulder height to set their drinks on. Jess rolled his sleeves up to his elbows. The blue neon made Rory's skin and his white dress shirt luminescent in the dark of the bar.

"Thanks for getting me out of the house," she said, honestly.

"That's what friends are for," he handed her a glass, and then raised his. "To Richard."

"To Grandpa," she echoed, softly, and clinked her glass against his.

They took a drink. In the harsh light of the neon, Rory looked exhausted. She had dark circles under her eyes, and looked more pale and drawn than usual.

"How's the book this week?" she asked.

Jess felt like his book didn't matter in the slightest, after she had buried her grandfather that morning, but he let her maintain the semblance of a normal day, a normal conversation. "Still terrible," he said. "I can't get it right. It's a miserable wreck."

"It's not a miserable wreck," she disagreed, swishing her whiskey in the glass. "It's beautiful. You just can't bring yourself to finish it."

There was some truth to her words. The fault lay with Jess, and he knew it.

"You know, once upon a time you wrote a book and couldn't end it," she said, lightly. "Sent it off to some girl to edit. _Thanks for making me bleed_ , you told me."

He smiled. "You've been editing it this whole time. There's a difference."

"Send me the whole thing," she suggested. "I've gotten it piece by piece, but I haven't read it in its entirety. I haven't seen the beginning chapters in a year. I'd love to try to visualize the whole arc, the whole story."

She made sense. But Jess felt uncomfortable at the thought of it. He knew it wasn't Rory's editorship that he needed it - this fight was not with a plot, with unruly characters, with uneven arcs or shoddy craftsmanship. This was an internal fight that Jess, at this point, seemed determined to lose. It wasn't a writing problem. It was an emotion problem.

"You're holding yourself back," she observed. He started when he realized that her blue eyes were on him again, too close in the loudness of the bar, too vivid in the bright of the neon sign. She sipped her whiskey.

"Maybe," he acknowledged.

"I don't understand why," Rory continued, gaze still fixed on him. "What are you trying to avoid?"

He felt his heart beating from its solitary confinement, and, like a familiar habit, gave an unaffected shrug. "No idea."

Jess didn't want to talk about this. It was too hard, with Rory a foot away from him. He didn't have the mental capacity to do all of this with her eyes on him, to keep himself locked up, to look casual and careless, to stop his mind from running rampant, to keep his heart rate low and his expression nonchalant. It was too much work.

Fatigued, he sipped his whiskey and changed the topic. "How's the new job?"

Rory gave him a sideways look, fully aware that he was rerouting the conversation on purpose, but let him get away with it. "It's been great. Hopefully I still have a job, after this week, but I've really been enjoying it. I have a few different authors I'm working with right now."

"What kind of authors?" He asked. He didn't have to feign too much interest. He _was_ interested in her life, and felt that odd twinge of pride again. It felt good to hear about Rory's success, and it reminded him of high school, of a young, sweet, gangly Rory, who talked about Harvard and journalism with the confidence of a girl who usually had all the right answers.

"Fiction mostly, a few novellas," she replied. "One poetry anthology - tell Matthew mine actually _will_ be a bestseller."

Jess smiled despite himself. "Tell him yourself. It'd be a good check on his ego."

Rory smiled. But her eyes were still sad. "I will."

He let the quiet stretch a moment, and took a sip of his whiskey. Rory leaned against the wall and looked out over the crowd, watching the revelry and the costumes but not really seeing them. She held her glass in her hand like an afterthought.

"How are you?" Jess asked, after a long pause. "Are you okay after this week?"

She sipped her whiskey. "I'm not sure."

The pauses in their conversation were punctured by bursts of laughter from other tables. As the night grew later, it was as if people couldn't help but shout their conversations. The din swelled around them, infectious, exhausting. Jess waited patiently.

"It's just so hard to believe he's really gone," Rory finally said, biting her lip. "It doesn't feel real. It feels like tomorrow morning I'll wake up and come downstairs and find him reading the newspaper. And he'll raise his eyebrows at me and ask what on earth happened last night to cause such a mess in the kitchen."

Jess nodded, understanding. He kept his eyes fixed on her small hand, dangling the whiskey glass.

"I'm not sure what this will do to Grandma," she continued, as if thinking out loud. "I can't imagine her in that big house by herself."

"It's a lot to manage," Jess agreed.

"It'll be so lonely," she furrowed her eyebrows, concern creeping into the lines of her face. "She won't come to Stars Hollow - it would kill Mom - but I don't know what she'll do."

Jess continued to be quiet, patient. Something about the noise of the bar, and probably the whiskey, made their closeness and the aura of melancholy feel intimate and isolated. He could tell there were groups pressing around them, but as they leaned against the bar, heads close together, nursing their whiskey, it seemed as though they existed in a bubble of quiet inside the rowdy space.

She looked down at the floor. "The last days were terrible, Jess."

"How so?"

Her shoulders moved in something between a shudder and a shrug. "He was so sick. Sometimes it would be like he was there - he'd say things to us, have moments of coherency, smile and laugh over some memory or other, give us some serious bit of advice. And sometimes it was like he was living in a different time, talking to his parents, or to his childhood friends. And most of the time he was asleep, his breath all weak and labored."

She painted a vivid picture, and Jess reacted to it with whiskey.

"I'm so sorry, Rory," he said, his voice low. He really meant it.

She took a drink too. Both of them were nearing empty. And then she glanced up at him with her eyes bright. "I know."

He dropped his gaze, but he felt hot. Jess couldn't look at her, not this close. He didn't want to see the brightness of her eyes, the tears that threatened but did not come.

Smooth as ever, he plucked her glass out of her hand. "More alcohol," he said, like it was the doctor's orders, and headed into the throng by the bar.

There was something deeply wrong with him, Jess decided, as he shouldered his way through the bodies and reached the edge of the bar. He shook his head, experimentally, but it didn't help. His heart was beating quickly, and he felt uncomfortably hot in his dress shirt and slacks. He couldn't handle that kind of closeness with Rory, the shocking blue of her eyes when she looked up at him through her eyelashes. Even when she was devastated, swallowed by grief - when he _should_ be a good friend and perfect gentleman - he felt himself anxiously burying his heart deeper into solitary confinement to prevent the internal racket. He could take the heat, the discomfort, the pain, but he didn't want an interior monologue explaining the reasoning behind his symptoms.

The bartender returned with their second round, and Jess gripped both glasses firmly. She needed a friend, and he needed to get his shit together.

"Here you go," he returned and handed Rory a glass, "answer to all life's problems."

She gave a faint half-smile in appreciation, and took a drink. "Think it'll actually solve life's problems? Or just make more?"

Jess knew whiskey was just causing more problems for him, but he ignored himself. "Whiskey solves everything, haven't you read Hemingway?"

"I might get very drunk tonight," she warned him, but she didn't sound serious.

"I'm planning on it," he said.

Rory clinked her glass against his, and drained half of it. Jess raised his eyebrows. Maybe she did mean it.

The night felt like a broken hourglass, time speeding up and slowing down at odd increments. Rory talked about everything, about her grandfather, about her Mom, about her job, about - Jess rolled his eyes - her latest dull ex boyfriend. She spun little narratives for him, a collection of observations and details and worries. When she mentioned Richard, or her mother and grandmother, she seemed to become quieter, swaying slightly in her heels, eyebrows pinched by sadness. But she alighted into grief for only short periods, meandering through less painful subjects and then dipping back into mourning.

Jess fully intended to switch to water after their second round, conscious of his car keys in his pocket and his responsibility for the woman next to him. But Rory would have none of it. She forced him to keep pace with her, promising to pay for a cab and let him sleep at her grandparents' house, swearing that it was essential that he did this with her. "Whiskey and sympathy only works both ways," she told him, like it was a well-known fact. "It doesn't work if you're taking care of me."

"Somebody has to," he said, amused.

"We'll take care of each other," she insisted. And pushed her glass towards him for a refill.

The night grew later and sloppier. And, as Jess expected, Rory began to let her guard down and slip into her grief. She clung to the edge - she gave him snarky one-liners, she made a few inappropriate jokes and pop culture references - but after their third (or fourth?) round, she began to drop her façade of responsibility. She rested her head back against the wall and looked up at him, devastated in that beautiful, delicate way that only Rory Gilmore could pull off.

He leaned one hand against the wall and looked out into the crowd. A few musketeers playing darts were laughing so hard that they had collapsed onto the floor, and a bachelorette party of Disney princesses were circled in a huddle of outrage after a Power Ranger had spilled a drink on one of them. He heard Rory sigh, only half a foot away from him.

"I can't do this, Jess," she said, tired.

"Do what?" he asked, barely glancing at her. He'd had too much whiskey. He couldn't look at her.

She seemed to hesitate, and then swallowed her response. With great effort, she lifted herself up from leaning against the wall and handed him her empty glass. "Let's do this properly."

Jess forced a slight smile, and did her bidding by going to the bar and collecting the next refill. This night was going to kill him.

The whiskey wore down Rory's self-defensive humor, her weightless, self-deprecating one-liners and references, giving way to a woman who closed her eyes against the loss and grief of her last week, her last year. She tried to explain it to Jess, shaping words to describe the mix of emotions that were festering inside her - grief, relief, sadness, nostalgia, guilt. And he nodded and listened and stayed close, head bowed towards hers in the corner of the bar, providing what sympathy and what support he could.

Her sadness, loosened free by the alcohol and the ending of her day responsibilities, began to suffocate her. She looked up at him, hopeless, a tear or two threatening to escape from the corners of her eyes. "I just can't believe he's gone," she whispered.

"Grief never makes any sense," Jess said, his voice soft.

"Yeah," she said, like an echo.

Jess continued talking to her, murmuring, his voice low beneath the din of the bar. He wasn't saying anything useful, but he could tell she needed the distraction - the sympathy. And she seemed to be fighting with herself, fighting against waves of grief or guilt or god knows what.

Rory turned sideways to face him. Doing so moved her closer to him, only six inches away or so, and he felt that familiar lurch in his stomach at the suddenness of seeing her bright blue eyes. Unfocused and distracted and overwhelmed as she was, she looked directly at him, torn by something different and deeper.

"I've been a mess lately," she told him, faintly.

"We're all messes sometimes," he shrugged. "Some of us more often than others."

She nodded in distracted agreement. "I'm not sure how to compartmentalize."

Of course she was thinking about compartmentalizing. Rory clung to rationality and reason, seeking organization and clarity even as she was rocked by loss. Jess smiled ruefully, "You can try, but you might have more success in the morning. Grief gets ugly at night."

"Grief gets ugly at night," she echoed, slowly.

"I mean that everything bad gets worse at night," Jess elaborated. "it all seems to get more hopeless. And then morning comes, and things get better."

Rory nodded, unfocused. "I can see that."

He could see her processing, see the waves that she was fighting as she swayed in place. If she wasn't leaning against the wall, he wasn't sure how long she'd be able to remain standing for. She seemed precariously close to dropping her glass simply by forgetting she was holding it.

A tear slipped down her cheek. Rory closed her eyes again, squeezing them shut, and another tear or two escaped. She bit her lip.

Jess sighed, and reached for her glass. She let go of it easily. He put both of their glasses on the ledge next to them and then reached for Rory's upper arm, rubbing his thumb in gentle, circular motions on her sleeve.

She leaned forward, one hand pulling on the fabric of his shirt near his hip, and he wrapped his arms around her. Her head buried in the crook of his neck, and he tightened his hold. Rory was quiet, not shaking or sobbing, but just holding on to him. Time felt like a heartbeat. And Jess closed his eyes, briefly, because it was all a bit too much and the whiskey was ruining him.

After a few minutes - or hours, Jess had no concept of time anymore - Rory pushed back, her face only a few inches from his. He felt himself reel, slightly, at being so close to her. He could see teardrops clinging to her eyelashes, her eyes searching him, troubled, distracted, indecisive.

Jess was too caught up in her gaze, too desperate to pull himself together, that he didn't realize what she was about to do until she raised on her toes and pressed her lips softly against his.

He spun - for a brief second, he lost his usual firm grasp on control and caution and reality. All of his alarm bells went off. That locked up teenage part of his heart beat ominously. And though he stood still, frozen, it felt like the floor dropped out from underneath him.

Rory was gentle. She pulled herself closer, both of her hands clutching the fabric of his shirt near his hips. Feather-light, she kissed his bottom lip, the corner of his mouth, his jaw line, his neck. When she returned her head to the crook of his neck, quiet, he could feel her wet eyelashes brushing against his skin.

He wrapped his arms around her more tightly, his thoughts racing. The noise of the bar swelled and pulsed around them. He felt like if he made one wrong step, that locked up part of his heart would break up and wreak havoc. Already it was straining, pressing, furious with him.

Jess wasn't an idiot. He might be overwhelmed by the clanging din of sirens and alarm bells that were going off internally, but he could see past the fight-or-flight racket to the woman in front of him who was searching for any kind of comfort. Although he had refused to think about it, he knew that she had been focused on him lately, knew that she was further than he was, knew that she had been pressing the boundaries of their friendship intentionally and recklessly in the last months. If he really stepped back and drew on the years of experience he had observing people and writing their emotional catastrophes, nothing Rory was doing was out of the ordinary. She was grasping for a lifeline to something real, reaching blindly in the dark for something to push away the grief, or maybe absorb the grief, and keep her feet on the ground. And - despite his rigid denial and whiskey anesthetics - she had been feeling for the cracks in their platonic foundation for months.

But, in this moment, Jess knew what she needed. He felt like he was outside of his body, watching the pair of them against the dark wall in the bar, watching Rory unravel and try to save herself by tangling him up in her loose threads. He saw his own role in this, and he sighed. Nothing about this was going to make his battle against himself any easier.

Gently, he drew his hands back and grasped her shoulders, moving her slightly, pulling her away from his body, creating those few, overwrought inches of space that had nearly cracked him before. She looked up at him, distraught and distant. He let his eyes meet hers, unwavering, even as he burned.

Jess moved his hands up to cradle her face, swiping away one tear with the pad of his thumb. Then he leaned in and pressed his lips to hers, seizing her grief with his kiss, giving her what she needed and ignoring the long term damage it was undoubtedly going to cause him.

 _And so it goes_.

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Dear readers, thank you for the reviews! They make my day better, they inspire me to pull up the word document and continue writing. The feedback has been so lovely.

This chapter marks a sharp shift in tone, mood, and plot development. The switch felt sudden, but I imagine tragic events often snarl timelines and expectations. Also, as the premise of this story indicates, every chapter marks a jump a few months or so into the future. I often have to account for how _much_ lives change over the course of so much time. So even though it felt like a leap to take this story into the gloom of tragedy and Halloween, after the lighthearted, dialogue-heavy, midsummer night's dream energy of the previous chapter, it also felt like the right and natural thing to do. This was challenging to write, but I hope you all enjoyed it.

More to come soon . . .


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